Month: July 2021

Synthetic Route of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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.

This was prepared as per 25e from 24 using t-butyl 4-bromobutanoate. Yield 21%. 1H NMR (300 MHz, CHLOROFORM-d) d7.18-7.33 (m, 3H), 7.09 (d,J= 6.78 Hz, 2H), 6.98 (br s, 1H), 6.87 (d,J= 8.29 Hz, 1H), 6.65-6.73 (m, 2H), 6.58-6.64 (m, 1H), 6.46 (dd,J= 2.17, 8.19 Hz, 1H), 6.33 (d,J= 2.07 Hz, 1H), 4.47 (dd,J= 8.01,14.98 Hz, 1H), 3.79 (s, 3H), 3.73 (s, 3H), 3.54-3.69 (m, 2H), 3.32-3.47 (m, 1H), 3.14 (t,J= 6.88 Hz, 2H), 3.07-3.32 (m, 2H), 2.76-2.99(m, 4H), 2.41-2.54 (m, 1H), 2.34 (t, J= 7.16 Hz, 2H), 1.90 (quin,J= 7.02 Hz, 2H), 1.46 (s, 9H).m/z588 (M+H)

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perrey, David A.; Decker, Ann M.; Li, Jun-Xu; Gilmour, Brian P.; Thomas, Brian F.; Harris, Danni L.; Runyon, Scott P.; Zhang, Yanan; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5709 – 5724;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-(3-bromophenyl)acetate

Step B:; To a solution of (3-bromophenyl) -acetic acid methyl ester 46 (1.20 g, 5.28 mmol) in dry dimethyl-acetamide (5 mL) is added under argon zinc cyanide (0.78 g, 6.64 mmol) and tetrakis(triphenylphosphine) palladium (0.63 g, 0.55 mmol). The mixture is stirred for 24 hours at 80C. After cooling to room temperature, the mixture is diluted with EtOAc (15 mL) and water (20 mL). The resulting precipitate is removed by vacuum filtration. The organic layer of the filtrate is separated and washed with H20, then dried over MgS04, filtered and concentrated. Purification by silica gel chromatography (0 to 20% EtOAc/hexane) to give (3-cyano-phenyl) acetic acid methyl ester 47 as an oil: ¹H-NMR (400MHz, CDCl3) 8 = 7.63 (d, J= 8.0 Hz, 1H), 7.47 (d, J= 1.2 Hz, 1H), 7.30 (dd, J= 1.2 Hz, J= 8.0 Hz, 1H), 3.72 (s, 3H), 3.69 (s, 2H). MS calculated for C10H9O2ClN (M+W) 210.0, found 210.0.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 150529-73-0.

Reference:
Patent; IRM LLC; WO2005/113519; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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 11.12b: Compound (5-33) KOH, THFZH2Oily-V-33[00438] 3-Methyl-2-(2-methyl~1H-indol-4’yloxy)-butyric acid ethyl ester (2): A mixture of 4-hydroxy-2-methylindoie (1) (1.5 g, 0.010 mole), 2-bromo-3-methyl-butyric acid ethyl ester (2.2 g, 0.010 mole) and potassium carbonate (excess) in acetone (50 mL) was refluxed for 3 days. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (20:1 Hex:EtOAc) to afford intermediate 2. Yield: 1.88 g, 71 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-bromo-3-methylbutanoate, its application will become more common.

Reference:
Patent; ILYPSA, INC.; WO2007/56279; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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. Formula: C8H8FNO2

Add in a 150 mL two-necked flask at room temperature 2-fluoro-4-aminobenzoic acid ester 2 (4.5 g, 26.6 mmol), acetone (2.99 g, 42.7 mmol), potassium cyanide (2.6 g, 40 mmol) and 46 mL of acetic acid, the mixture was heated to 75 C for 24 h, and the reaction was monitored by TLC ( petroleum ether: ethyl acetate = 20:3). After the reaction was completed, 20 mL of water was added to the reaction mixture, and ethyl acetate (40×3 mL) was evaporated.The residue was dissolved by adding a mixed solvent of 6 mL of ethanol and 5 mL of water. cooling crystals, filtering to give compound 21, 3.13 g, yellow solid, yield 50.2%.

The synthetic route of 73792-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changsha Zeda Pharmaceutical Technology Co., Ltd.; Chen Yongheng; Xu Guangyu; Zhou Wenqiang; (23 pag.)CN108976171; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

40061-54-9, name is Ethyl 2-(2-chlorophenyl)acetate, 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. Computed Properties of C10H11ClO2

1. Take 100 ml of a dry single-mouth flask, and add 2-chloro-phenylacetic acid ethyl ester (1 g, 0.0054 mmol in 10 ml of methanol, then place the system in an ice bath and slowly add lithium aluminum hydride (0.41 g, 0.0108 mmol). ), continue to stir for 1 h after the additionAfter the reaction is completed, a small amount of water is added for quenching.Thereafter, methanol was removed under reduced pressure and extracted with 15 ml of ethyl acetate.After washing with saturated brine, the extract phase was collected and dried over anhydrous sodium sulfate overnight.After the end of drying, the solvent was removed under reduced pressure to give a colorless oil, Compound A,It was used directly in the next reaction without purification.

The synthetic route of 40061-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin International Bio-pharmaceutical Joint Institute; Nankai University; Wang Ying; Cai Yan; Mao Yonghong; Guo Yu; Yu Zhenwu; Yang Yang; Zhao Peipei; He Wanli; (10 pag.)CN109897007; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 10 liter glass reactor, 2080 g of a yellow oily liquid obtained in the above step and 4L of a 6 M hydrochloric acid solution were added. The reaction was carried out for 3 h at room temperature, and HPLC detection showed that the starting material had reacted completely. The reaction mixture was concentrated to dryness, neutralized with 1M sodium hydroxide solution to neutral, and concentrated again to dryness, samples were dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give a colorless oil 1650g. HPLC analysis showed a product purity of 97% and a total reaction yield of 91%

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 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu Jinsirui Biological Technology Co., Ltd.; Shen Junwei; Zhang Fangliang; Zhang Jianqi; Luo Fulin; (11 pag.)CN109096128; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, 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.

To a solution of pyridine-3-carbothioamide (1 g, 7.24 mmol) in EtOH (15 mL) and pyridine (1 mL, 12.3 mmol) was added methyl 2-bromobutanoate (1 mL, 8.68 mmol). The mixture was heated at reflux for 18 hours, after which it was cooled and concentrated. The crude 5-Ethyl-2-pyridin-3-yl-thiazol-4-ol was then redissolved in DMF (36 mL) at 0 C., and to the mixture was added 60% sodium hydride (751 mg, 18.8 mmol). After stirring for 15 min at rt, 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide (3.87 g, 10.8 mmol) was added. The mixture was reacted for 20 min, quenched with sat. NH4Cl, diluted with diethyl ether. The mixture was washed with water, and then brine. The organic layer was concentrated, and the resulting material chromatographed (5-55% EtOAc/Hexanes to give trifluoro-methanesulfonic acid 5-ethyl-2-pyridin-3-yl-thiazol-4-yl ester (0.85 g) as an orange oil.

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Jo; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Thakkar, Kshitij Chhabilbhai; Wilhelm, Robert Stephen; US2013/158066; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 935273-86-2,Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, 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 solution of benzyl 3,3-difluorocyclobutanecarboxylate (1.4 g, 6.2 mmol) in ethanol (50 mL) was added palladium on activated carbon (500 mg) and the reaction mixture was stirred at RT under an atmosphere of hydrogen (1 atm) for 12 h. The reaction mixture was filtered through a pad of CELITE and the filtrate was concentrated to afford Intermediate 291A as pale yellow liquid (550 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 12.97-12.76 (m, 1H), 3.04-2.91 (m, 1H), 2.89-2.64 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Benzyl 3,3-difluorocyclobutanecarboxylate, its application will become more common.

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-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.

1.0016 g (8.1358 mmol) of pyridine-4-carboxylic acid dissolvedin 10 mL of thionyl chloride was stirred and refluxed for 3 h. Then1.3423 g (8.1258 mmol) of methyl-4-amino-3-methylbenzoate wasadded in 35 mL of chloroform into the precipitated acid chloride. The reaction mixture was heated with stirring for another 2 h and ayellow powder precipitated.2.2500 g (7.3351 mmol, yield ca.: 90%, Anal. Cal. C15H15Cl1N2O3[%]: C, 58.73; H, 4.93; N, 9.13; Found: C, 58.57; H, 4.66; N, 9.13) ofobtained powder was filtered and washed with chloroform anddiethyl ether. The yellow needles precipitated after recrystallizationfrom acetonitrile/MeOH solution mixture. 1H NMR (600 MHz,MeOD) delta 10.61 (s, 1H), 9.14-9.06 (m, 1H), 8.56 (d, J 6.5 Hz, 1H),7.99 (dd, J 1.4, 0.4 Hz, 1H), 7.92 (dd, J 8.3, 1.7 Hz, 1H), 7.65 (d,J 8.3 Hz, 1H), 3.92 (s, 1H), 2.41 (s, 1H). 13C NMR (151 MHz, MeOD)delta 168.16, 163.71, 152.05, 144.43, 140.80, 135.13, 133.23, 129.95,128.93, 127.12, 126.99, 52.83, 18.36. FT-IR (KBr, cm1): 3436 n(O-HKBr), 3241 n(N-H), 3170, 3105, 3053, 3010, 2955, 2866 n(C-H),1712, 1689 n(C]O), 1633-1434 n(ringC]C), 1315e1139 n(C-O) and(C-N) overlapped, 840, 770, 647 d(C-H ringC]C)oop.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Skokowski, Przemys?aw; Gruszczy?ska, Joanna; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1178; (2019); p. 669 – 681;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 25542-62-5, name is Ethyl 6-bromohexanoate, A new synthetic method of this compound is introduced below., Safety of Ethyl 6-bromohexanoate

To a solution of triphenylphosphine (918 mg, 3.5 mmol) in MeCN (5 mL) was added 6-bromohexanoic acid ethyl ester (669 muL, 3.0 mmol). The mixture was refluxed for 7 h and concentrated. The residue was purified by silica gel column chromatography to give the target compound (1.14 g, 78%) as a white foam.1H NMR (500 MHz, CDCl3) delta: 7.89-7.85 (m, 6H), 7.81-7.78 (m, 3H), 7.72-7.68 (m, 6H), 4.07 (q, 2H, J = 7.3 Hz), 3.95-3.89 (m, 2H), 2.27 (t, 2H, J = 7.3 Hz), 1.76-1.72 (m, 2H), 1.66-1.58 (m, 4H), 1.22 (t, 3H, J = 7.3 Hz). FAB-MS m/z: 405 [M-Br]+.

The synthetic route of 25542-62-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Motoshima, Kazunori; Ishikawa, Minoru; Hashimoto, Yuichi; Sugita, Kazuyuki; Bioorganic and Medicinal Chemistry; vol. 19; 10; (2011); p. 3156 – 3172;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics