Category: 109232-37-3

Some common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, molecular formula is C11H21ClO2, 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

Compound 1-1 (4-chloro-2,5-dimethylphenol) (780 mg, 5.0 mmol), 5-chloro-2,2-dimethylvaleric acid isobutyl ester (1144 mg, 5.2 mmol), TBAI (36.9mg, 0.1mmol), potassium carbonate (1380mg, 10.0mmol) was dissolved in DMF (30mL), and stirred at 90 C overnight. TLC monitors the tendency of discontinuous conversion. The reaction solution is poured into water and the layers are separated. After the aqueous phase is extracted with ethyl acetate, the organic phases are combined, dried over anhydrous sodium sulfate, filtered and the filtrate is concentrated. Compound 1-2 (1.5 g) was isolated by analysis and the yield was 88%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109232-37-3, its application will become more common.

Reference:
Patent; Beijing Hou Shenyaode Science And Technology Co., Ltd.; Jiao Ning; Yu Siwang; Song Song; Liu Yameng; Yang Simin; (60 pag.)CN110857268; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 109232-37-3,Some common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, molecular formula is C11H21ClO2, 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 phenol (5 mmol) was added to a solution of sodium (114 mg, 5 mmol) in absolute EtOH (5 mL) at room temperature. After stirring for 30 min, a solution of suitable ethyl or isobutyl ester (5-bromovalerate, 5-bromo-2,2-dimethylpentanoic acid ethyl ester or 5-chloro-2,2-dimethylpentanoic acid isobutyl ester) (5 mmol) in absolute EtOH (5 mL) was added and the solution was stirred at reflux for 10-15 h. The solvent was removed under reduced pressure and the residue was dissolved into CH2Cl2 or ethyl acetate (25 mL) and washed with NaOH 2 N (3 × 25 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product that was purified by column chromatography to give the ester 9-14, 16 or 25-31. Ester 15 was obtained with the same procedure, but under milder conditions: K2CO3 (1.1 g, 8.38 mmol) was added to a solution of N-(4-hydroxyphenyl)-N’-phenylurea (531 mg, 2.33 mmol) in acetone (10 mL) at room temperature. After stirring for 30 min, a solution of ethyl 5-bromovalerate (488 mg, 2.33 mmol, 0.37 mL) in acetone (10 mL) was added. After 30 h the solvent was removed under reduced pressure and the residue was treated as above to give the compound 15.

The synthetic route of 109232-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Filippis, Barbara; Giancristofaro, Antonella; Ammazzalorso, Alessandra; D’Angelo, Alessandra; Fantacuzzi, Marialuigia; Giampietro, Letizia; MacCallini, Cristina; Petruzzelli, Michele; Amoroso, Rosa; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 5218 – 5224;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, 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. 109232-37-3

5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (136 mg, 0.28 mmol) and isobutyl 5-chloro-2,2-dimethylpentanoate (124 mg, 0.56 mmol) are dissolved in DMA (1 mL) and Cs2C03 (183 mg, 0.56 mmol) and Nal (42 mg, 0.28 mmol) added. The mixture is microwaved at 150 C for 20 min then diluted with water and extracted with EtOAc (3 x20 mL). The organic is then washed with Brine (10 mL) and dried over Na2S04 and concentrated. HPLC purification gives 70 mg (38% yield) of alkylated product isobutyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6- yl)methylsulfonamido)-2,2-dimethylpentanoate. MS-ES [M + H]+ = 670.2. This compound is used directly in the next step.

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 109232-37-3.

Reference:
Patent; NOVARTIS AG; BARNES, David; CHOPRA, Rajiv; COHEN, Scott Louis; FU, Jiping; KATO, Mitsunori; LU, Peichao; SEEPERSAUD, Mohindra; ZHANG, Wei; WO2011/131709; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics