Esters-buliding-blocks

Synthetic Route of 23426-63-3, A common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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: Toa solution of 1a (770 mg, 3.24 mmol) in DMF (20 mL) was added potassium carbonate (2.69g, 19.5 mmol).Thereaction mixture was stirred at ambient temperature for 30minutes. After addition of ethyl bromoacetate (1.08mL), the mixture was heated at 70oC for 2 hours. The mixture was cooled to ambient temperature andwater (60 mL) was added. The solution was extractedwith ethyl acetate (3 30 mL). The organic phase was washed withsaturated aqueous sodium chloride solution (2 ¡Á 15mL), dried over sodium sulfate, filtered and concentrated. The residue waspurified by column chromatography (silica gel, petroleum ether/ethyl acetate 5:1)to give the title compound (464 mg, 44% yield) as white solid.

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:
Article; Huang, Yaping; Sun, Geng; Wang, Pengfei; Shi, Rui; Zhang, Yanchun; Wen, Xiaoan; Sun, Hongbin; Chen, Caiping; Bioorganic and Medicinal Chemistry Letters; vol. 28; 17; (2018); p. 2957 – 2960;,
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Application of 15012-36-9, A common heterocyclic compound, 15012-36-9, name is Methyl 2,3-dimethylbenzoate, molecular formula is C10H12O2, 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.

Methyl 2,3-dimethylbenzoate was dissolved in concentrated sulfonic acid (10 mL). KNO3 (808 mg, 1.2 eq.) was added to the solution at 0 C., then slowly warmed to rt overnight. The reaction was quenched with water (80 mL), extracted with ethyl acetate (2¡Á80 mL). The organic layers were evaporated to give mixture of nitrated ester and acid (1:1). The mixture was redissolved in DMF (10 mL). K2CO3 (1.1 g) and iodomethane (0.5 mL) were added to the solution. The reaction was stirred at rt for three days, then diluted with water (80 mL). It was extracted with ethyl acetate (3¡Á80 mL) and evaporated. The residue was purified by column chromatography (EtOAc in hexanes=0-30% in 45 min) to give the desired nitrobenzoate ester. 1H NMR (300 MHz, DMSO) delta 8.31 (s, 1H), 8.24 (s, 1H), 3.86 (s, 3H), 2.46 (s, 3H), 2.40 (s, 3H).

The synthetic route of 15012-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; US2012/28923; (2012); A1;,
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Some common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, molecular formula is C3H3F3O2, 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: 431-47-0

General procedure: Amixture of carbazole 5-h (0.68 mmol) and THF (15 ml)was stirred and treated by the addition of LiH (0.03 g,3.40 mmol) and methyl trifluoroacetate (0.26 g,2.03 mmol). The reaction mixture was stirred for 1.5-5 h at63, evaporated, and treated with cold 5% hydrochloricacid solution (20 ml). The precipitate was filtered off,washed with water, and then dried over P2O5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 431-47-0, its application will become more common.

Reference:
Article; Pugachov, Dmitriy E.; Kostryukova, Tatiana S.; Zatonsky, Georgy V.; Vatsadze, Sergey Z.; Vasil?ev, Nikolai V.; Chemistry of Heterocyclic Compounds; vol. 54; 5; (2018); p. 528 – 534; Khim. Geterotsikl. Soedin.; vol. 54; 5; (2018); p. 528 – 534,7;,
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Application of 18595-18-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound (1b) 10.00 g (0.06 mol), cyanamide 5.08 g (0.12 mol),50 mL of ethanol was charged and the temperature was raised to 70 C. After dropping 7.12 g (0.07 mol) of concentrated sulfuric acid over 6 hours, the mixture was stirred under reflux for 2 hours.After the completion of the reaction, the reaction mass was cooled to 5 C., kept warm, filtered,Washed with 40 mL of ethanol. The obtained crystals were dried under reduced pressure,14.53 g (yield 93.7%) of 1/2 sulfate of the compound (2b) was obtained.LC area percentage 100%

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, Methyl 3-amino-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Kumazawa, Hiroharu; Nishimori, Nobuaki; Okura, Yuka; (15 pag.)JP2020/2108; (2020); A;,
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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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H13BrO2

To a stirred mixture of 3-[(methylamino)methyl]benzonitrile (6.1 g, 41.7 mmol) and sodium bicarbonate (7.0 g, 83.4 mmol) in ACN (70 mL) was added dropwise tert-butyl 3-bromo- propanoate (7 mL, 41.7 mol). After being stirred at RT for 12 hours, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSOd6, 400 MHz) delta 7.70 (s, 2H), 7.60 (m, 1 H), 7.51 (m, 1 H), 3.49 (s, 2H), 2.58 (m, 2H), 2.36 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

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; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
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Reference of 6933-47-7, 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. 6933-47-7 name is Methyl 4-amino-2-methylbenzoate, 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.

General procedure: Step (viii): Methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate. A suspension of 217 3-chloro-4-ethoxy 5-isopropoxybenzoic acid (48: R2=iPr, R3=Et) (2.82g, 10.9mmol) and 145 methyl 4-amino-2-methylbenzoate (38: R1=Me) (2.16g, 13.1mmol) in 45 ethyl acetate (33mL) was treated with 46 triethylamine (4.56mL, 32.7mmol) followed by 44 T3P (50wt% in ethyl acetate) (17.34mL, 27.3mmol) and the mixture was heated at 60C for 4h and allowed to cool to room temperature for 16h. The reaction mixture was stirred vigorously with an aqueous solution of 218 sodium hydrogencarbonate (50mL) for 10min and separated. The aqueous layer was extracted with dichloromethane (3¡Á100mL) and the combined organic phases were dried (magnesium sulfate), filtered concentrated in vacuo and the residue purified by silica gel chromatography (40g, 0:50:50 to 20:40:40 ethyl acetate:120 dichloromethane:isohexane) to produce 219 methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate as a beige solid (3.24g, 70% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-2-methylbenzoate, and friends who are interested can also refer to it.

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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935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, 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. name: Benzyl 3,3-difluorocyclobutanecarboxylate

Intermediate 296A: Benzyl 3,3-difluoro-1-methylcyclobutanecarboxylate To a solution of benzyl 3,3-difluorocyclobutanecarboxylate (2 g, 8.84 mmol) and MeI (2.202 mL, 35.4 mmol), in THF (15 mL) at -78 C. under a N2 atmosphere was added a solution of KHMDS (35.4 mL, 17.68 mmol, 0.5 M in toluene). The reaction mixture was then stirred at -78 C. for 6 h after which it was allowed to warm to RT and stir overnight. The reaction mass was then quenched with a saturated aq. solution of NH4Cl and extracted with diethyl ether (3*25 mL). The combined organic fractions were washed with water, dried over Na2SO4, filtered and concentrated under vacuum. The crude product was purified by silica gel chromatography (40 g REDISEP column, eluting with 20% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford the Intermediate 296A as a pale yellow liquid (1.2 g, 56.5%). 1H NMR (400 MHz, chloroform-d) delta ppm 7.50-7.23 (m, 5H), 5.17 (s, 2H), 3.22-2.97 (m, 2H), 2.60-2.28 (m, 2H), 1.51 (s, 3H).

The synthetic route of 935273-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Synthetic Route of 61367-07-5, These common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate 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.

Example 19(1r,4R)-4-(2-phenyl-1H-indole-6-sulfonamido)-N-((R)-1-(pyridin-2-yl)ethyl)cyclohexanecarboxamide Step 1. Preparation of (1r,4r)-methyl 4-(4-chloro-3-nitrophenylsulfonamido)cyclo hexanecarboxylate; (1r,4r)-methyl 4-aminocyclohexanecarboxylate HCl salt (7.75 g, 40 mmol) was suspended in a mixture of DCM (50 mL) and then treated with triethylamine (22.31 mL, 160 mmol), followed by 4-chloro-3-nitrobenzene-1-sulfonyl chloride (11.27 g, 44 mmol). The reaction mixture was stirred at rt for 2 h and then concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with 1N aq. HCl (3¡Á100 mL), brine (100 mL) and dried over sodium sulfate. Filtration and concentration of the organic solution gave product (14.1 g) as a yellow solid (MS: (M+H)+=377.3).

The synthetic route of 61367-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; US2012/28969; (2012); A1;,
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Related Products of 24807-40-7,Some common heterocyclic compound, 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, molecular formula is C17H18O3, 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.

Methyl 2-((4-((phenylmethyl)oxy)phenyl)methyl)butanoate(32.1).; To a solution of lithium diisopropylamide (6.5 mL, 2.0 M in heptane/THF/ethylbenzene) in THF (25.0 mL) and l,3-dimethyl-3,4,5,6- tetrahydro-2(lH)-pyrimidinone (5.0 mL) was added methyl 3-(4- (benzyloxy)phenyl)propanoate 23.1 (3.00 g, 1 1 mmol) in THF (1OmL) and 1,3- dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (2.5 mL) at -780C. The resulting mixture was stirred at -780C for 30 minutes and then iodoethane (1.0 mL, 13 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL), and the mixture was concentrated in vacuo. The residue was disolved in EtOAc (100 mL), washed with brine (2×25 mL), and dried with Na2SO4. The residue was purified by silica gel column (eluent with hexane/EtOAc; 85/15) to give the title compound 32.1. MS ESI (pos.) m/e: 299.0 (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 Methyl 3-(4-(benzyloxy)phenyl)propanoate, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/130514; (2008); A1;,
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Application of 541-16-2, 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. 541-16-2, name is Di-tert-Butyl malonate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cooled(0 C) solution of NaH (60% in mineral oil, 2.2 eq.) in DMF (1.0 M) was slowly added di-t-butylmalonate (1.1 eq.). After 15 min, 2-fluoronitrobenzene derivative (5.00 g) was added to the reactionmixture dropwise at 0 C. The resultant mixture was stirred at room temperature overnight and quenchedwith 0.1 N HCl aq. The resultant aqueous phase was extracted with EtOAc/n-hexane = 1/1. The combinedorganic phases were washed with brine. The resultant organic phase was dried over Na2SO4, filtered, andthe filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography(n-hexane/EtOAc = 100/0 – 30/70).

The chemical industry reduces the impact on the environment during synthesis Di-tert-Butyl malonate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yamai, Yu-Suke; Tanaka, Akio; Yajima, Tatsuo; Ishida, Kyoji; Natsutani, Itaru; Uesato, Shinichi; Nagaoka, Yasuo; Sumiyoshi, Takaaki; Heterocycles; vol. 97; 1; (2018); p. 192 – 210;,
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