methyl 4-isopropylcyclohexanecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】11701

【品名】methyl 4-isopropylcyclohexanecarboxylate

【CA登记号】

【分子式】C₁₁H₂₀O₂

【分子量】184.2786

【元素组成】C 71.7% H 10.94% O 17.36%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

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

Extended Information