ethyl 2-[[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]amino]-4-phenylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】27321

【品名】ethyl 2-[[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]amino]-4-phenylbutanoate

【CA登记号】

【分子式】C₂₂H₂₇NO₄

【分子量】369.46072

【元素组成】C 71.52% H 7.37% N 3.79% O 17.32%

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：(XI)

The condensation of (IX) with alanine benzyl ester (X) with sodium cyanoboohydride as before gives N-[1-(ethoxycarbonyl)-3-phenylpropyl]alanine benzyl ester (XI), which is submitted to fractional crystallization with maleic acid yielding N-[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine benzyl ester (XII), which is debenzylated by hydrogenation with H2 over Pd/C in ethanol yielding the free acid (XIII). Finally, this compound is condensed with spirane (IV) through the N-hydroxysuccinimide ester, in the usual way.

参考文献中间体

合成目标

【1】 Smith, E.M.; Neustadt, B.R.; Gold, E.H. (Schering Corp.); 7-Carboxyalkylaminoacyl-1,4-dithia-7-azaspiro[4.4]-nonane-8-carboxylic acids. JP 1989163197; US 4470972 .
【2】 Prous, J.; Castaner, J.; Spirapril. Drugs Fut 1987, 12, 9, 860.

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)	23808	Fumaric acid; (E)-2-butenedioic acid	110-17-8	C₄H₄O₄	详情	详情
(IV)	27316	methyl (8S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylate		C₈H₁₃NO₂S₂	详情	详情
(IX)	20896	Ethyl 2-oxo-4-phenylbutanoate; 2-Oxo-4-phenylbutyric acid ethyl ester	64920-29-2	C₁₂H₁₄O₃	详情	详情
(X)	10143	benzyl (2S)-2-aminopropanoate		C₁₀H₁₃NO₂	详情	详情
(XI)	27321	ethyl 2-[[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]amino]-4-phenylbutanoate		C₂₂H₂₇NO₄	详情	详情
(XII)	15665	ethyl (2S)-2-[[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]amino]-4-phenylbutanoate		C₂₂H₂₇NO₄	详情	详情
(XIII)	11360	(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]propionic acid; (S)-N-(1-Ethoxycarbonyl-3-phenylpropyl)-(S)-alanine	82717-96-2	C₁₅H₂₁NO₄	详情	详情

Extended Information