4-Isopropylcyclohexanecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】11702

【品名】4-Isopropylcyclohexanecarboxylic acid

【CA登记号】

【分子式】C₁₀H₁₈O₂

【分子量】170.25172

【元素组成】C 70.55% H 10.66% O 18.79%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The hydrogenation of 4-isopropylbenzoic acid (I) with H2 over PtO2 in acetic acid gives 4-isopropylcyclohexanecarboxylic acid as a mixture of cis- and trans-isomers (II). This mixture is esterified with methanol to the corresponding mixture of methyl esters (III), which is isomerized with NaH at 150 C without solvent, affording the trans-methyl ester (IV). Hydrolysis of (IV) with NaOH in methanol - water gives the free acid (V), which is finally condensed with D-phenylalanine (VI) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in chloroform.

参考文献中间体

合成目标

【1】 Toyoshima, S.; Seto, Y.; Shinkai, H.; Toi, K.; Kumashiro, I. (Ajinomoto Co., Inc.); Hypoglycemic agent. EP 0196222; US 4816484 .
【2】 Shinkai, H.; Dan, K.; Toi, K.; Kumashiro, I.; Seto, Y.; Toyoshima, S.; Nishikawa, M.; Fukuma, M.; Sato, Y.; N-(Cyclohexyl)carbonyl-D-phenylalanines and related compounds. A new class of oral hypoglycemic agents. 2. J Med Chem 1989, 32, 7, 1436.
【3】 Prous, J.; Graul, A.; Castaner, J.; AY-4166. Drugs Fut 1993, 18, 6, 503.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11698	4-Isopropylbenzoic acid	536-66-3	C₁₀H₁₂O₂	详情	详情
(II)	11699	4-Isopropylcyclohexanecarboxylic acid		C₁₀H₁₈O₂	详情	详情
(III)	11700	methyl 4-isopropylcyclohexanecarboxylate		C₁₁H₂₀O₂	详情	详情
(IV)	11701	methyl 4-isopropylcyclohexanecarboxylate		C₁₁H₂₀O₂	详情	详情
(V)	11702	4-Isopropylcyclohexanecarboxylic acid		C₁₀H₁₈O₂	详情	详情
(VI)	11703	D-Phenylalanine; (R)-Phenylalanine	673-06-3	C₉H₁₁NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Chen SN, Feng QJ, Yu YM, et aL 2007. Preparation of H type nateglinide crystal.发明专利申请公开说明书．CN 1887858 (Hangzhou Pollen Co, Ltd, Peop Rep China)
【2】 Wang D, Liang YH, Gang P,et aL 2002.A new synthesis method of nateglinide as antidiabetic drug. 中国药物化学杂志，12 (2): 94～96
【3】 Yahalomi R 2004. Process for preparing nateglirude and intermediates thereof. W0 2004005240[本专利为Teva Pharmaceutical Industries Ltd (IL)-所有]
【4】 Zhu XY, Peng K, Wang XQ, et aL 2001. Synthesis of nateglinide.合成化学,9(6): 537～540

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11702	4-Isopropylcyclohexanecarboxylic acid		C₁₀H₁₈O₂	详情	详情
(II)	66534	4-isopropylcyclohexanecarbonyl chloride		C₁₀H₁₇ClO	详情	详情
(III)	11703	D-Phenylalanine; (R)-Phenylalanine	673-06-3	C₉H₁₁NO₂	详情	详情

Extended Information