Category: esters-buliding-blocks

Synthetic Route of 1139-13-5,Some common heterocyclic compound, 1139-13-5, name is Diethyl cyclohexane-1,1-dicarboxylate, molecular formula is C12H20O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1. To a solution of compound 18-1 (4.0 g, 17.5 mmol) in EtOH (20 mL) was added 85% aqueous KOH solution (1.15 g, 17.5 mmol) at r.t. After the reaction mixture was stirred at 76 C for 3 h, it was concentrated and partitioned between EtOAc (15 mL) and H20 (25 mL). The aqueous phase was acidified with IN HC1 to pH = 3 and extracted with EtOAc (15 mL x 2). The organic layer was concentrated to give compound 18-2 as an oil (2.5 g, yield: 71.4%). ‘H NMR (400 MHz, CDC13) delta 4.20 – 4.15 (m, 2 H), 2.03 – 1.90 (m, 4 H), 1.56 – 1.47 (m, 6 H), 1.45 – 1.43 (t, 4.0 Hz, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl cyclohexane-1,1-dicarboxylate, its application will become more common.

Reference:
Patent; GENENTECH, INC.; THE UNIVERSITY OF AUCKLAND; LEE, Ho Huat; TERCEL, Moana; FLYGARE, John A.; GUNZNER-TOSTE, Janet; PILLOW, Thomas H.; SAFINA, Brian; STABEN, Leanna; VERMA, Vishal; WEI, BinQing; ZHAO, Guiling; WO2015/95227; (2015); A2;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 344-14-9 as follows. Computed Properties of C5H7FO4

A mixture of 2-fluoro-4-amidinopyridine hydrochloride (1.17 g, 6.662 mmol), dimethyl fluoromalonate (1 g, 6.662 mmol), DBU (3.35 mL, 22.4 mmol) and MeOH (50 mL) was stirred at room temperature overnight. The crude reaction mixture was evaporated under reduced pressure to yield a brown oil. A 2 N HC1 solution was cautiously added and the precipitate was collected by filtration, washed with water and dried in a vacuum oven to give the title compound (0.992 g, 66% yield). LCMS: RT 2.91 min, MI 225, Method (4LCMS1).

According to the analysis of related databases, 344-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; CARSWELL, Emma, L.; CHARLES, Mark, David; COCHI, Anne; DUGAN, Benjamin, J.; EKWURU, Chukuemeka, Tennyson; ELUSTONDO, Fred; FOWLER, Katherine, M.; LEROUX, Frederic, Georges, Marie; MONCK, Nathaniel, J.T.; OTT, Gregory, R.; ROFFEY, Jonathan, R.; SIDHU, Gurwinder; TREMAYNE, Neil; (305 pag.)WO2018/55402; (2018); A1;,
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These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of Methyl 2,2-dimethoxyacetate

Cyclohexanone Compound 2a (1.37 g, 14.0 mMol) in THF (5 mL) was added dropwise to a solution of LHMDS (16.0 mL, 16.0 mMol) in anhydrous THF (25 mL) at -78 C. under a N2 atmosphere. The solution was stirred at -78 C. for about 1 hr. Methyl dimethoxyacetate Compound 11a (1.88 g, 14.0 mMol) in anhydrous THF (5 mL) was then added dropwise. The reaction mixture was stirred while warming to r.t. over a period of about 15 hrs, then the reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford 2-(2,2-dimethoxy-acetyl)-cyclohexanone Compound 11b (1.82 g, 65%). Benzylhydrazine dihydrochloride Compound 11c (1.75 g, 9.00 mMol) and K2CO3 (1.51 g, 10.92 mMol) were added to a solution of Compound 11b (1.80 g, 9.10 mMol) in MeOH (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred overnight while warming to r.t., then the reaction was quenched with water (20 mL). The organic layer was diluted with EtOAc (200 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 20% EtOAc in hexane) to afford 1-benzyl-3-dimethoxymethyl-4,5,6,7-tetrahydro-1H-indazole Compound 11d (1.80 g, 70%) as a colorless oil. 3N HCl (8 mL) was added to a solution of Compound 11d (1.70 g, 5.9 mMol) in acetone (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred for 4 hrs while warming to r.t., then the reaction was quenched with water (20 mL), neutralized to pH 7 with K2CO3 and diluted with CH2Cl2 (100 mL). The organic layer was washed with water and brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford a 1-benzyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 11e (1.35 g, 95%) as a colorless oil. Methanesulfonyl chloride Compound 11f1 (2.0 g, 17 mMol) and TEA (2.43 mL, 17.46 mMol) were added to a solution of (1R)-1-phenyl-ethylamine Compound 11f2 (1.75 g, 17.5 mMol) in CH2Cl2 (50 mL) at 0 C. under a N2 atmosphere. The mixture was stirred for 3 hrs while warming to r.t., then the reaction was quenched with water (5 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford the corresponding N-(1-phenyl-ethyl)-methanesulfonamide Compound 11f3 as an oil. (Boc)2O (di-tert-butyldicarbonate) (4.57 g, 21.0 mMol) and DMAP (8 mg) were added to a solution of the methanesulfonamide Compound 11f3 in CH2Cl2 (10 mL) at 0 C. under a N2 atmosphere. The mixture was stirred overnight while warming to r.t., then the reaction was quenched with a saturated solution of NaHCO3 (sodium bicarbonate) (10 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude Boc-protected methanesulfonamide product. The product was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford (methylsulfonyl)[(1R)-1-phenyl-ethyl]-carbamic acid tert-butyl ester Compound 11f (3.89 g, 80%) as a colorless oil. Adapting a published procedure (Tozer M J, Woolford A J A and Linney I A, Synlett, 1998, 2, 186-188) to obtain the target compound, a 1M solution of KOtBu (potassium tert-butoxide) in THF (0.75 mL, 0.75 mMol) was added dropwise to a solution of the ester Compound 11f (0.070 g, 0.250 mMol) in anhydrous THF (5 mL) at -78 C. under a N2 atmosphere. After 45 min, Compound 11e (0.060 g, 0.250 mMol) diluted in THF (3 mL) was added dropwise. The solution was reacted over a 15 hr period while warming to ambient temperature. The reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and then washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product. The product was purified by flash chromatography (eluted with 20% EtOAc in hexane) to give Compound 260 (0.079 g (75%), as a white solid. MS m/z 422 (MH+); 1H NMR (CDCl3, 400 MHz) delta 7.56 (d, J=15.5 Hz, 11H), 7.35-7.19 (m, 8H), 7.11-7.09 (m, 2H), 6.42 (d,J=15.5 Hz, 1H), 5.21 (s, 2H), 4.61-4.11 (m, 2H), 2.45-2.41 (m, 2H), 2.36-2.33 (m, 2H), 1.75-1.67 (m, 4H), 1.55 (d, J=6.5 Hz, 3H).

The synthetic route of Methyl 2,2-dimethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lagu, Bharat; Liotta, Fina; Pan, Meng; Wachter, Michael P.; Xia, Mingde Xia; US2005/228034; (2005); A1;,
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These common heterocyclic compound, 64123-77-9, name is Methyl 2-(3-fluorophenyl)acetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of Methyl 2-(3-fluorophenyl)acetate

General procedure: The oil was thendissolved in EtOH, and NH2NH2.H2O (3 eq) was added.The mixture was refluxed for 10 h. CH2Cl2 (30 mL) was thenadded and extracted with distilled H2O (3 × 20 mL). Theorganic phase was separated, dried on anhydrous Na2SO4,and evaporated under vacuum to afford correspondinghydrazide 7a in very good yield (white solid, 1.02g, 93%)

The synthetic route of Methyl 2-(3-fluorophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vu, Vu Van; Nhung, Trinh Thi; Thanh, Nguyen Thi; Chinh, Luu Van; Tien, Vu Dinh; Thuy, Vu Thu; Thi Thao, Do; Nam, Nguyen Hai; Koeckritz, Angela; Vu, Tran Khac; Journal of Chemistry; vol. 2017; (2017);,
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Related Products of 57486-67-6,Some common heterocyclic compound, 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, molecular formula is C9H9FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Sodium hydride (1427 g, 35.7 mmoi) was added to a solution of methyl 2-(-fiuorophenyl)acetate(2 g, 1189 mmoi) in TIfF (20m1) at 0 C and allowed to stir at same temperature for 30 mi Methyliodide (5.21 ml, 83 mrnoi) was added dropwise and reaction mixture was stirred at RT for overnight. The reaction mixture was neutralized with saturated ammoniurn chloride and extracted with ethyl acetate (2x150m1). Combined organic phase was washed with brine, dried with anhydrous sodium sulfate and evaporated to give methyl 2-( -fluorophenyl)-2-methyipropanoate (1.5 g, 7.64 mrnol, 64.3 % yield) as oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-(2-fluorophenyl)acetate, its application will become more common.

Reference:
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
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Application of 541-16-2, These common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of di-tert-butyl malonate (4.3 g, 19.91 mmol, 1.99 equiv) and potassium carbonate (2.8 g, 20.29 mmol, 2.03 equiv) in N,N-dimethylformamide (30 mL) was stirred at 65C for 30 min. A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol- 2-yl)benzoate (2.65 g, 10.00 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) was then added dropwise with stirring to the reaction mixture. The resulting solution was stirred at 65C overnight and then quenched with 60 mL of ice and water. The mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 3×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 4.0 g (90%) of methyl 4-(4-(3-tert-butoxy-2-(tert- butoxycarbonyl)-3-oxopropyl)-5-methyloxazol-2-yl)benzoate as a light yellow solid. LC-MS: (ES, m/z): 446 [M+H]+, 390, 334, 272, 230, 115.

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; RUGA CORPORATION; GIACCA, Amato; LAI, Edwin; RAZORENOVA, Olga; CHAN, Denise; HAY, Michael, Patrick; BONNET, Muriel; SUN, Connie; TABIBIAZAR, Ray; YUEN, Po-wai; WO2013/155338; (2013); A2;,
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Reference of 4630-80-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4630-80-2 name is Methyl cyclopentanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A 2.5 M solution of BuLi in hexane (2.77 mmol; 1.1 ml; 1.2 eq) is added at -10 C. to a solution of DIPA (diisopropylethylamine) (3 mmol; 1.3 eq; 420 mul) in THF (9 ml) under inert atmosphere. The mixture is stirred for 1 hour at 0 C. This LDA solution, freshly prepared, is added dropwise to a solution of cyclopentanoic acid methyl ester in 5 ml of THF at -55 C. The mixture is stirred for 1 hour at -55 C. under inert atmosphere. HMPA (hexylmethylphophoramide) (3.46 mmol; 1.5 eq; 610 mul) is added and the mixture is stirred for 10 minutes at the same temperature. A solution of 4-methoxybenzyl mercaptan disulfide (3 mmol; 1.3 eq; 920 mg) in 12 ml of THF is then added dropwise at -55 C. After returning to room temperature, the mixture is stirred overnight. The mixture is partitioned between 10 ml of saturated NH4Cl and 20 ml of AcOEt. The organic phase is washed with saturated NH4Cl (2×10 ml), saturated NaCl (2×15 ml), dried on Na2SO4 and then concentrated under reduced pressure to yield the crude product which is purified by chromatography on silica gel. (0262) C(R2R3)=Cyclopentyl: oil (Yield: 40%) (0263) HPLC: Atlantis T3, CH3CN (0.1% TFA)/H2O (0.1% TFA) Gradient 30-90% 10 min, Rt=9.68 min (0264) NMR (CDCl3, 200 MHz): 1.60-2.40 (8H, m); 3.67 (3H, s); 3.77 (2H, s); 3.80 (3H, s); 6.83 (2H, d); 7.24 (2H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl cyclopentanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMALEADS; ROQUES, Bernard Pierre; FOURNIE-ZALUSKI, Marie-Claude; PORAS, Herve; US2015/299116; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: Methyl 2,4-difluorobenzoate

Under a nitrogen atmosphere,1H-pyrrolo[2,3-b]pyridin-5-ol (1.0 g, 7.45 mmol), Methyl 2,4-difluorobenzoate (1.6 g, 9.31 mmol), Potassium phosphate (2.05g, 9.69mmol)Add to 20mL diglyme solution,The reaction solution was stirred at 115 C for about 10 h.Plate analysis until the starting material is completely reacted.The reaction solution was cooled to room temperature, then quenched with water and ethyl acetate.Collect organic phase,Purification by column chromatography gave a white solid product (1.3 g).The yield was 62%.

The synthetic route of Methyl 2,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Liu Zhiqiang; (35 pag.)CN108658983; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 581065-95-4, name: tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

To a stirred solution of 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)- picolinic acid (08) (200 mg, 0.44 mmol, 1.0 equiv) in DMF (5.0 mL, 25.0 vol. equiv), were added tert-butyl l-amino-3,6,9, 12-tetraoxapentadecan-15-oate (165 (171.0 mg, 0.53 mmol, 1.2 equiv), HATU (505 mg, 1.33 mmol, 3.0 equiv) and DIPEA (68.50 mg, 0.53 mmol, 1.20 equiv). The reaction mixture was stirred for 12 h at RT. Completion of the reaction was monitored by TLC. The Reaction mixture was quenched with DMW (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic extract was washed with brine (100 mL), dried over Na2S04 and concentrated under vacuum to afford the titled compound (16) (160 mg, 47.90%) as a brownish gum. MR (300 MHz, OMSO-d6) delta 9.23 (s, 1H), 9.02 (s, 1H), 8.75 (s, 1H), 8.52- 8.51 (d, 1H), 8.13-8.12 (d, 1H), 7.64-7.63 (d, 2H), 7.61 (s, 1H), 7.58 (s, 1H), 7.38-7.37 (d, 1H), 7.19-7.16 (m, 3H), 3.58-3.44 (m, 18H), 2.51-2.49 (t, 2H), 1.38 (s, 9H). MS (ES+): 755.0 (M+l); MS (ES-): 753.3 (M-l). HPLC: 97.56%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; QUARTZ THERAPEUTICS, INC.; ZAMBONI, Robert; HENNING, Ryan; JI, Alan; SMITH, Tyler; HELLER, Bradley; REDDY, Thumkunta Jagadeeswar; ROCHELEAU, Sylvain; BEAULIEU, Marc Andre; (266 pag.)WO2018/200981; (2018); A1;,
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Related Products of 5941-55-9,Some common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, molecular formula is C7H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of ethyl-(E)-3-ethoxyacrylate (21 mmol) and 2N NaOH (12 mL) was refluxed for 2 h. The solution was then evaporated to dryness. The residue was redissolved in toluene (7 mL), the solution stirred for 3 min and the solvent evaporated. This was repeated 5 times until water was removed from the solid which was used directly in the next step. S?um (E)-3- ethoxyacrylate (3.30 mmol) (20) was added to thionyl chloride (15.2 mmol) and the mixture was refluxed for 90 min. The solution was evaporated and the residue was dissolved in dry THF, 2 mL).4′-met’oxy-[1,1′-biphenyl]-2-amine (2.19 mmol) and pyridine (5.0 mmol) were added to the solution at 0 C. Resulting mixture was stirred for 18h at room temperature. Next, water/EtOAc was added to the solution and the aqueous phase was separated and washed with EtOAc. The organic phase was dried with Na2SO4, evaporated and the residue was purified on silica chromatography to give the sub-title product. Yield: 43%

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; JORGENSEN, William L.; DZIEDZIC, Pawel; CISNEROS, Jose; (240 pag.)WO2016/130968; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics