benzyl (2S,3aR,7aS)-1-((2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propanoyl)octahydro-1H-indole-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】19516

【品名】benzyl (2S,3aR,7aS)-1-((2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propanoyl)octahydro-1H-indole-2-carboxylate

【CA登记号】98677-37-3

【分子式】C₃₁H₄₀N₂O₅

【分子量】520.66908

【元素组成】C 71.51% H 7.74% N 5.38% O 15.36%

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：(V)

The esterification of (3aR,7aS)-octahydroindole-2(S)-carboxylic acid (I) with benzyl alcohol (II) by means of SOCl2 gives the corresponding benzyl ester (III), which is condensed with N-[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (IV) by means of 1-hydroxybenzotriazole, N-ethylmorpholine and dicyclohexylcarbodiimide (DCC) in DMF giving the benzyl ester (V) of the desired product. Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in ethanol.

参考文献中间体

合成目标

【1】 Ubach, H.; Henning, R.; Teetz, V.; Geiger, R.; Becker, R.; Gaul, H. (Aventis SA); Novel bicyclic amino acid derivs., process for their preparation and their use , as well as bicyclic amino acids as intermediates and process for their preparation. DE 3151690; EP 0084164; EP 0170775; JP 1989301659; JP 1989301695 .
【2】 Prous, J.; Castaner, J.; TRANDOLAPRIL < Rec INN >. Drugs Fut 1989, 14, 8, 778.

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)	19512	(2S,3aR,7aS)octahydro-1H-indole-2-carboxylic acid	145438-94-4	C₉H₁₅NO₂	详情	详情
(II)	18710	Benzyl alcohol; Phenylmethanol	100-51-6	C₇H₈O	详情	详情
(III)	19514	benzyl (2S,3aR,7aS)octahydro-1H-indole-2-carboxylate	144540-71-6	C₁₆H₂₁NO₂	详情	详情
(IV)	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
(V)	19516	benzyl (2S,3aR,7aS)-1-((2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propanoyl)octahydro-1H-indole-2-carboxylate	98677-37-3	C₃₁H₄₀N₂O₅	详情	详情

Extended Information