2-[1-(2-methoxy-2-oxoethyl)cyclohexyl]acetic acid -Drug Synthesis Database

【结构式】

【分子编号】30544

【品名】2-[1-(2-methoxy-2-oxoethyl)cyclohexyl]acetic acid

【CA登记号】

【分子式】C₁₁H₁₈O₄

【分子量】214.26152

【元素组成】C 61.66% H 8.47% O 29.87%

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：(V)

Reaction of cyclohexenone (I) with ethyl cyanoacetate (A) in the presence of ammonia affords the Guareschi salt (II), which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid (III). The anhydride (IV) can be treated either with methanol to yield the halfester (V), or with hydroxylamine to afford the N-hydroxyimide (VII). The halfester (V) is subjected to a Curtius type rearrangement to give the isocyanate (VI), which is hydrolyzed to the amino acid hydrochloride (Xl).

参考文献中间体

合成目标

【1】 Satzinger, G.; Hartenstein, J. (Pfizer Inc.); Cyclic sulphonyloxyimides. DE 2611690; ES 457050; FR 2344540; GB 1575709; JP 52113977; US 4152326 .
【2】 Satzinger, G.; Hartenstein, J.; Herrmann, M.; Heldt, W. (Pfizer Inc.); Cyclic aminoacids. DE 2460891; ES 443723; FR 2294697; GB 1465229; JP 51088940; US 4024175 .
【3】 Castaner, J.; Serradell, M.N.; Gabapentin. Drugs Fut 1984, 9, 6, 418.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	11877	Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate	105-56-6	C₅H₇NO₂	详情	详情
(I)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(II)	30541	3',5'-Dicyano-2',4'-dioxospiro[cyclohexane-1,4'-piperidide] ammonium salt		C₁₂H₁₆N₄O₂	详情	详情
(III)	30542	2-[1-(2-hydroxy-2-oxoethyl)cyclohexyl]acetic acid	4355-11-7	C₁₀H₁₆O₄	详情	详情
(IV)	30543	3-oxaspiro[5.5]undecane-2,4-dione		C₁₀H₁₄O₃	详情	详情
(V)	30544	2-[1-(2-methoxy-2-oxoethyl)cyclohexyl]acetic acid		C₁₁H₁₈O₄	详情	详情
(VI)	30545	methyl 2-[1-(isocyanatomethyl)cyclohexyl]acetate		C₁₁H₁₇NO₃	详情	详情
(XI)	30546	2-[1-(aminomethyl)cyclohexyl]acetic acid	60142-96-3	C₉H₁₇NO₂	详情	详情

Extended Information