Category: esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Product Details of 110661-91-1

[000730] To a solution of Example 1.2.7 (0.103 g) and tert-butyl 4-bromobutanoate (0.032 g) in dichloromethane (0.5 inL) was added N,N-diisopropylethylamine (0.034 mL) at 50 C in a sealed amber vial overnight. The reaction was concentrated, dissolved in dimethyl sulfoxide/methanol (1 : 1, 2 mL) and purified by reverse phase HPLC using a Gilson system, eluting with 5-75% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. MS (ESI) m/e 944.6 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; TAO, Zhi-Fu; DOHERTY, George; WANG, Xilu; SULLIVAN, Gerard M.; SONG, Xiaohong; KUNZER, Aaron R.; WENDT, Michael D.; MARIN, Violeta L.; FREY, Robin R.; CULLEN, Steve C.; WELCH, Dennie S.; SHEN, Xiaoqiang; BENNETT, Nathan B.; HAIGHT, Anthony R.; ACKLER, Scott L.; BOGHAERT, Erwin R.; SOUERS, Andrew J.; JUDD, Andrew S.; (623 pag.)WO2016/94509; (2016); A1;,
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Some common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, molecular formula is C10H17NO2, 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-aminobicyclo[2.2.2]octane-1-carboxylate

At RT, 258 mg (1.41 mmol) of methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 402 mg (1.06 mmol) of HATU and 182 mg (1.41 mmol) of DIPEA were added to a solution of 210 mg (0.71 mmol) of 6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid in 5 ml of DMF. The mixture was then stirred at 60 C. for 1 h. After cooling to RT, the mixture was added to 20 ml of a 10% strength citric acid solution. The resulting precipitate was filtered off, washed with water and dried under reduced to pressure. This gave 326 mg (97% of theory, purity 98%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.48 (s, 1H), 8.05 (d, 1H), 7.77 (dd, 1H), 7.66 (d, 1H), 7.60-7.47 (m, 5H), 3.59 (s, 3H), 2.32 (s, 3H), 2.09-2.00 (m, 6H), 1.91-1.82 (m, 6H). LC/MS (Method 1, ESIpos): Rt=1.22 min, m/z=463 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 135908-33-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEININGHAUS, Mark; TERJUNG, Carsten; MUENSTER, Uwe; OLENIK, Britta; (92 pag.)US2018/36300; (2018); A1;,
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Related Products of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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.

General procedure: A solution of the 4 (0.48 g, 2 mmol), 3-fluoroaniline (0.24g,2.2 mmol) in isopropanol (30 ml) were stirred at 90 C for 4 h.Isopropanol was removed under reduced pressure and the residuewas purified through a column chromatography on silica withchloroform/methanol (V:V 50:1) as a white solid (0.58 g, 91.8percentyield).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Huai-Wei; Deng, Cheng-Long; Li, Dan-Dan; Liu, Dan-Dan; Chai, Shao-Meng; Wang, Wei; Zhang, Yan; Chen, Kai; Li, Xin; Wang, Jian; Song, Shao-Jiang; Song, Hong-Rui; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 460 – 470;,
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Related Products of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

Part A: 5-Fluoro-4,6-dihydroxy-2-methylpyrimidine A solution of 200 ml. of 25% wt sodium methoxide in methanol (0.84 mol) was diluted with an additional 200 ml. of methanol. Acetamidine-HCI (40 g , 0.42 mol) was added to the sodium methoxide solution (white precipitate formed), followed by addition of dimethyl fluoromalonate (70 g, 0.46 mol). The contents were stirred at room temperature overnight, then concentrated in vacuo to dryness. The resulting residue was redissolved in hot water (300 ml_). After cooling the aqueous solution to room temperature, concentrated HCI was added slowly until crystal formation (fine white prisms) took place at about pH 5. Concentrated HCI was added dropwise until pH 3, and then the contents were filtered. The isolated crystals were rinsed with 1 M HCI and dried under vacuum to provide 5-fluoro-4,6-dihydroxy-2-methylpyrimidine (65.5 g, >100%). LCMS: (M+H)+: 145.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
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Some common heterocyclic compound, 25415-67-2, name is Ethyl 4-methylpentanoate, molecular formula is C8H16O2, 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. category: esters-buliding-blocks

EXAMPLE 37 (FROM TABLE 1) 5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic Acid (3-diethylaminopropyl)amide A mixture of 2-aminoacetophenone hydrochloride (1 equiv.), ethyl isobutylacetate (1.2 equiv.) and sodium acetate (2.4 equiv.) in H2O was stirred at 100 C. for 18 hours and then cooled to room temperature. The aqueous layer was decanted off and the oil was dissolved in ethyl acetate. It was then washed with water and brine and then dried to give (93%) of 2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester as a red brown oil. 1H NMR (300 MHz, DMSO-d6) delta 11.21 (s, br, 1H, NH), 7.14-7.27 (m, 5H), 6.70 (d, J=2.7 Hz, 1H), 4.02 (q, J=7.1 Hz, 2H, OCH2CH3), 3.65 (m, 1H, CH(CH3)2), 1.22 (d, J=7.5 Hz, 6H, CH(CH3)2), 1.04 (t, J=7.1 Hz, 3H, OCH2CH3). MS-EI m/z 257 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25415-67-2, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Related Products of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: 3-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 muL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRADSHAW, Curt W.; Sakamuri, Sukumar; Fu, Yanwen; Oates, Bryan; Desharnais, Joel; Tumelty, David; US2009/98130; (2009); A1;,
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Application of 33993-24-7,Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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 20 g (136 mmol) 1 ,3,5-triazine-2,4-diamine hydrochloride (GAS-No of free base:504-08-5), 500 mL water and 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was stirred for 1 day at RT. 20 g (130 mmol) cyclopropanecarbonylcyclopropanecarboxylate was added into the reaction and stirring was continued for 1 day at room temperature. Another batch of 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was added and stirring was continued for 3 days at room temperature. The above procedure was repeated once and the solutions of two batch reaction were combined. The solids were filtered off and the crude product purified by FlashPrep-HPLC (column: 018 silica gel; mobile phase, ACN/water (0.05% NH4OH) =5% increasing to ACN/water (0.05% NH4OH)=20% within 12 mm; Detector, UV 254 nm) to give10.5 g (22%) of the title compound.LC-MS: m/z = 180 [M÷H].

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
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Synthetic Route of 28868-76-0, A common heterocyclic compound, 28868-76-0, name is Dimethyl 2-chloromalonate, molecular formula is C5H7ClO4, 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.

To a suspension of K2CO3 (49.3 G) in acetone (100 ml) a solution of 2-chloro-5- methoxy-phenol (37.7 G, boiling point 83-86C, 13 mbar, [9]) was added dropwise at 40C. The dropwise addition of dimethyl CHLOROMALONATE (43.6 G) in acetone (100 ml) followed. The mixture was refluxed for 16 h before the solvent was removed under reduced pressure. The residue was taken up in water (400 ML) and extracted twice with DCM (400 ML). The organic extracts were dried over MGS04 and evaporated. Upon treatment of the oily residue with diethyl ether, the product crystallised. The crystals were collected, washed with a mixture of diethyl ether and hexane and dried to give 2- (2-chloro-5-methoxy-phenoxy)-malonic acid dimethyl ester (53.73 g) as white crystals. (CDC13) : 3.76 (s, 3H), 3.86 (s, 6H), 5.20 (s, 1 H), 6.53-6. 58 (m, 2H), 7.24-7. 29 (m, 1 H).

The synthetic route of 28868-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2004/50640; (2004); A1;,
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Related Products of 23426-63-3,Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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 B; 2,5-Dimethyl-4-thiocyanato-phenol 82 (5.75 g, 32.1 mmol) is dissolved in acetonitrile (25 mL) . Powdered cesium carbonate (15.32 g, 47.0 mmol) is added. Then 2-bromo-2- methyl-propionic acid methyl ester (4.50 mL, 34.8 mmol) is added and the mixture is stirred at 600C for 18 h. Filtration and concentration, followed by silica gel chromatography (0- 50% ethyl acetate in hexanes) yielded 2- (2, 5-dimethyl-4- thiocyanato-phenoxy) -2-methyl-propionic acid methyl ester 83 as an oil: 1H-NMR (400 MHz, CDCl3) (rotamers are present; the data given is for the most abundant isomer) delta = 7.39 (s, IH), 6.50 (S, IH), 3.78 (s, 3H)7 2.42 (s, 3H), 2.20 (s, 3H), 1.62 (s, 6H). MS calcd. for C14H17NNaO3S (M+Na+) 302.1, found 302.1.

The synthetic route of 23426-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/56366; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1731-79-9, These common heterocyclic compound, 1731-79-9, name is Dimethyl dodecanedioate, 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.

To a cooled (0 C) solution of LiAlH4 (1.73 g, 45.6 mmol) in THF (280 mL) was added a solution ofdimethyl dodecanedioate (4.35 g, 15.2 mmol) in THF (20 mL) dropwise, and the resulting solution wasstirred at 0 C for 3 h. Then, the reaction mixture was quenched with MeOH and 1 M HCl. The organic layer wasseparated and the aqueous layer was extracted with diethyl ether three times. The combined organic layer was washedwith water and brine, and dried over sodium sulfate. After evaporation of the solvent, the product was obtained(3.22 g, 92%) in high purity, which was then used in the next step without further purification.1H-NMR (500 MHz, CDCl3): delta3.64 (t, J =7.5 Hz, 4H, 1-H, 14-H), 1.57 (m, 4H, 2-H, 13-H), 1.35-1.26(20H, 3-H to 12-H)13C-NMR (125 MHz, CDCl3): delta63.1 (C1, C14), 32.8 (C2, C13), 29.6, 29.6, 29.5, 29.4 (C4 to C11), 25.7(C3, C12)HR-MS (ESI-TOF): m/z calcd for C14H30O2Na [M+Na]+ 253.2138, found 253.2137IR (film): 3409, 3347, 2923, 2854 cm

The synthetic route of 1731-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tonoi, Takayuki; Kawahara, Ryo; Yoshinaga, Yutaka; Inohana, Takehiko; Fujimori, Keiko; Shiina, Isamu; Tetrahedron Letters; vol. 56; 11; (2015); p. 1356 – 1359;,
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