Category: esters-buliding-blocks

Synthetic Route of 59247-47-1, 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 59247-47-1 as follows.

To a 250 mL round-bottom flask ‘.vas added (lS,4R,5R)-5-[[5-cyclopropyl-3-(2-cyclopropyl-6-fluoropheny)-1,2-oxazol-4-y l]methoxy ]-2-azabicyclo[2.2.1]heptan-3-one10 3lle (300 mg, 0.78 mmol, 1.00 equiv.), Pd1(dba)3 (36 mg, 0.04 mmoL 0.05 equiv.),XantPhos (46 mg, 0.08 mmol, 0.10 equiv.), Cs£03 (384 mg, 1.18 mmol, 1.50 equiv.), tol (5mL), and tert-hutyl 4-bromobenzoate (301 mg, 1.17 mmol, 1.50 equiv.). The resultingmixture vvas heated at ll0°C ovemight ·with stirring. After cooling to room temperature, themixture vvas diluted with 50 mL ofH20, extracted with ethyl acetate (100 mL x 2), and the15 combined organic extracts were washed with brine (100 mL x 2), dried, and concentrated.The residue was purified by silica gel column chromatography eluting with ethylacetate/hexane (2: l) to give tert-butyl 4-[(l S,4R,SR)-5-[[ 5-cyclopropyl-3-(2-cyclopropyl-6-fluorophenyl)-1,2-oxazol-4-yl]methoxy ]-3-oxo-2-azabicyclo[2.2.1 ]heptan-2-yl]benzoate 311 f(300 mg, 68percent) as a yellow oil.

According to the analysis of related databases, 59247-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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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 55666-43-8 as follows. Quality Control of tert-Butyl 3-bromopropanoate

Example 6; 7V-Benzyl-3-(4-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-l,2-dihydroquinolin-5- yl)ethyl]amino}piperidin-l-yl)propanamide; i) tert-Butyl 3-(4-oxopiperidin-l-yl)propanoate o To a solution of piperidin-4-one (1 g) in CHCl3 (30 mL) was added fert-butyl 3- bromopropanoate (1.2 mL) followed by triethylamine (1.8 mL). The reaction mixture was heated at reflux for 18 h. The mixture was allowed to cool to room temperature then diluted with EtOAc and H2O and the layers separated. The aqueous material was extracted with further EtOAc (x2) then the combined organic extracts washed with water followed 5 by saturated aqueous NaCl, collected and dried (MgSO4). The volatiles were removed in vacuo to afford the sub-title compound as an orange oil. Yield: 0.92 g 1H NMR (CDCl3) delta 2.81 – 2.75 (m, 6H), 2.47 – 2.42 (m, 6H), 1.46 (s, 9H).

According to the analysis of related databases, 55666-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/102771; (2007); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 426-65-3, name is Ethyl Pentafluoropropionate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl Pentafluoropropionate

Pentafluoroethyl cyclopropylethynyl ketone, (XVI) can be synthesized in an analogous fashion using ethyl pentafluoropropionate in the above reaction.

According to the analysis of related databases, 426-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pierce, Michael Ernest; Radesca, Lilian Alicia; US6348616; (2002); B1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 35179-98-7, name is Chloromethyl ethyl carbonate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H7ClO3

EXAMPLE 2 Preparation of 4-fluoro-2-[[(4-methoxy-2-pyridinyl)methyl] sulfinyl]-1H-benzimidazole-1-ylmethyl ethyl carbonate To NaOH (0.26 g, 6.5 mmol) dissolved in H2 O (12 ml) 4-fluoro-2-[[(4-methoxy-2-pyridinyl) methyl]sulfinyl]-1H-benzimidazole (1.0 g, 3.3 mmol) and tetrabutylammoniumhydrogen sulfate (1.1 g, 3.2 mmol) were added under stirring. The mixture was stirred for about 5 min, at ambient temperature and then extracted 3 times with CH2 Cl2 (20 ml). After separation the combined CH2 Cl2 phases were dried over Na2 SO4, filtrated and the solvent evaporated off giving an oil. The residual oil was dissolved in toluene (30 ml). Chloromethyl ethyl carbonate (0.68 g, crude material) dissolved in dry toluene (3 ml) was added under a protective gas and under stirring. The mixture was stirred at ambient temperature over night. The toluene was evaporated off and the residual oil was chromatographed on a silica column using ethyl acetate as eluent. Crystallizing from ethyl acetate – diethyl ether gave the title compound (0.33 g, 25%). NMR data for the product is given below.

According to the analysis of related databases, 35179-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aktiebolaget Hassle; US5049674; (1991); A;,
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383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C4H5ClF2O2

tert-Butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate A mixture of tert-butyl 5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-hydroxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1.00 g, 2.13 mmol), chlorodifluoroacetic acid ethyl ester (2.700 mL, 21.29 mmol), K2CO3 (882.7 mg, 6.387 mmol) and DMF (40 mL, 500 mmol) was heated to 70 C. for 6 h in a sealed tube. The material was extracted with EtOAc, and washed with water (3*). The organic layer was purified via column chromatography, eluting with 3-10% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a light yellow solid. 1H NMR (400 MHz, CD3OD): delta=1.67-1.69 (m, 9H), 1.80 (d, J=7.1 Hz, 3H), 4.94-5.03 (m, 1H), 6.63 (s, 1H), 7.15 (dd, J=9.1, 4.5 Hz, 1H), 7.22-7.28 (m, 1H), 7.55 (d, J=2.0 Hz, 1H), 7.70 (d, J=1.5 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H). MS (ES+): m/z=519.03/521.03 (75/100) [MH+]. HPLC: tR=1.93 min (polar-3 min, HPLC-ACQUITY).

The synthetic route of 383-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI Pharmaceuticals, LLC; US2011/281888; (2011); A1;,
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Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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. Application In Synthesis of Methyl 4-amino-2-methylbenzoate

General procedure: A solution of (7: R1=cyclopentyloxy) (100mg, 363mumol) in dichloromethane (5 mL), cooled to 0C, was treated with oxalyl chloride (63.6 muL, 727 mumol), followed by a drop of N,N-dimethylformamide. The resultant mixture was stirred for 1h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (5 mL) and then treated with a solution of methyl 4-aminobenzoate (8: R2=H, R=Me) (54.9mg, 363mumol) and di-isopropylethylamine (190muL, 1.09mmol) in dichloromethane (5mL). The reaction mixture was stirred for 12 h at room temperature and then partitioned between dichloromethane (20 mL) and aqueous 1M hydrochloric acid (20 mL). The phases were separated, and the organic phase was washed successively with water (2×20 mL), and brine (20 mL), dried over magnesium sulfate, filtered and then the solvent was removed in vacuo. The residue was purified by silica gel chromatography (12 g, 0-100 % ethyl acetate/isohexane) to afford methyl 4-[3,5-dichloro-4-(cyclopentyloxy)benzamido]benzoate (10: R1 = cyclopentyloxy, R2 = H, R =Me) (30mg, 20% yield). 1H NMR (400MHz, CDCl3) delta 8.06 (2H, d, J=8.8Hz,), 7.85 (1H, br s), 7.82 (2H, s), 7.71 (2H, d, J=8.8Hz), 5.07-5.03 (1H, m), 3.92 (3H, s), 2.10-1.90 (4H, m), 1.85-1.70 (2H, m), 1.70-1.60 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6933-47-7, its application will become more common.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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Related Products of 49851-36-7, These common heterocyclic compound, 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, 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.

ln a 40 mL vial, HATU (2.263 g, 5.95 mmol) was added in one portion at room temperature to a DMF solution (10 mL) of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (1g, 4.96 mmol), 6-chloropyridine-2-carboxylic acid (CAS 4684-94-0) (0.938 g, 5.95 mmol) and DIEA (2.165 mL, 12.40 mmol). The resulting solution was allowed to stir at room temperature (2.5 hr). The reaction was diluted with ethyl acetate, washed with water (twice) and a saturated aq. NaCI solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified via FCC (10:1 Heptane/ethyl acetate to 1 :1 Heptane/ethyl acetate) to give the title compound. MS (ESI+) m/z 305.3 (M+H).

Statistics shows that Methyl 2-(2-aminophenyl)acetate hydrochloride is playing an increasingly important role. we look forward to future research findings about 49851-36-7.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 75567-84-9

General procedure: Methyl 3-(4-bromophenyl)propanoate31 1 (1.0 equiv) and the appropriate commercially available (substituted-phenyl)boronic acid (1.5 equiv) were dissolved in a mixture of dioxane/EtOH (1:1) (concentration 1 mL/mmol) and 1 M aqueous NaHCO3 (2.0 equiv). To the solution, Pd(PPh3)4 (2.5 mol %) was added and the mixture was heated in the microwave at 100 C for 3 h, after which TLC showed full conversion. The reaction mixture was concentrated in vacuo, acidified to pH = 1 using 1 M HCl (aq), extracted with EtOAc, dried over MgSO4 and concentrated under reduced pressure. Purification by column chromatography eluting with CH2Cl2/Pet. ether (2:1) yielded the desired biphenyl esters as solids.

The synthetic route of 75567-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Veldhoven, Jacobus P.D.; Liu, Rongfang; Thee, Stephanie A.; Wouters, Yessica; Verhoork, Sanne J.M.; Mooiman, Christiaan; Louvel, Julien; Ijzerman, Adriaan P.; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 4013 – 4025;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-bromo-4-fluorobenzoate

Cesium carbonate ((3.1 g, 9.6 mmol) was added to 2,4-difluorophenol (0.83 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol)In a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was subjected to column chromatography (peel ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(2,4-difluorophenoxy)benzoate (1.58 g, 4. 72%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Sun Changan; Zhang Xiaoyu; Chen Gangsheng; Zong Shumin; (45 pag.)CN109836385; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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 252881-74-6, Computed Properties of C13H27NO5

To a solution of 5-hexynoic acid (100 mg, 893 mumol), WSC (257 mg, 1.34 mmol),HOBt (205 mg, 1.34 mmol) and DIPEA (622 muL, 3.60 mmol) in dry DMF (2 mL) wasadded tert-butyl-12-amino-4,7,10-trioxadodecanoate (297 mg, 1.34 mmol). The reactionmixture was stirred for 19 h at room temperature. After evaporation under reducedpressure, the reaction mixture was diluted in AcOEt and washed with sat NaHCO3 aq.,water and brine, and dried over Na2SO4. After filtration and evaporation gave compound3-5 (313 mg, 0.84 mmol, 68%) as a colorless oil.

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Reference:
Article; Takaoka, Yousuke; Uchinomiya, Shohei; Kobayashi, Daichi; Endo, Masataka; Hayashi, Takahiro; Fukuyama, Yoshiaki; Hayasaka, Haruko; Miyasaka, Masayuki; Ueda, Takumi; Shimada, Ichio; Hamachi, Itaru; Chem; vol. 4; 6; (2018); p. 1451 – 1464;,
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