ethyl (2S)-3-[[3-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoyl]amino)propanoyl]amino]-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate -Drug Synthesis Database

【结构式】

【分子编号】26623

【品名】ethyl (2S)-3-[[3-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoyl]amino)propanoyl]amino]-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate

【CA登记号】

【分子式】C₂₉H₃₉N₅O₈S

【分子量】617.72356

【元素组成】C 56.39% H 6.36% N 11.34% O 20.72% S 5.19%

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：(XIII)

The reaction of N-(benzyloxycarbonyl)-L-asparagine (I) with bis(trifluoroacetyl)iodobenzene (BTI) in DMF/water gives 3-amino-2(S)-(benzyloxycarbonylamino)propionic acid (II), wehich is protected at the amino group with tert-butoxycarbonyl anhydride yielding carbamate (III). The esterification of (III) with ethanol WSC and DMAP affords the expected ethyl ester (IV), which is selectively deprotected with methanesulfonic acid in acetonitrile providing 3-amino-2-(benzyloxycarbonylamino)propionic acid ethyl ester (V). The condensation of (V) with N-(tert-butoxycarbonyl)-beta-alanine (VI) by means of HOBT, WSC and triethylamine in DMF gives the protected propionamidopropionic ester (VII), which is selectively deprotected by hydrogenation with H2 over Pd/C in ethanol/ethyl acetate giving the 2-aminopropionic ester (VIII). The condensation of (VIII) with 4-ethylbenzenesulfonyl chloride (IX) by means of triethylamine in dichloromethane yields the sulfonamide (X), which is deprotected with methanesulfonic acid as before afording intermediate (XI) with a free amino group, which is condensed with 4-(tert-butoxycarbonylamino)benzoic acid (XII) by means of HOBT and WSC in DMF providing the fully protected target compound (XIII).

参考文献中间体

合成目标

【1】 Ikeda, Y.; Ueki, Y.; Kishimoto, H.; Nishihara, T.; Kamikawa, Y. (Sumitomo Pharmaceuticals Co., Ltd.); 2,3-Diaminopropionic acid deriv.. US 5707994; US 6048854; WO 9511228 .

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)	14529	(2S)-4-amino-2-[[(benzyloxy)carbonyl]amino]-4-oxobutyric acid	2304-96-3	C₁₂H₁₄N₂O₅	详情	详情
(II)	18008	(2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propionic acid; N(alpha)-Z-L-2,3-diaminopropionic acid	35761-26-3	C₁₁H₁₄N₂O₄	详情	详情
(III)	26613	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-[(tert-butoxycarbonyl)amino]propionic acid		C₁₆H₂₂N₂O₆	详情	详情
(IV)	26614	ethyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[(tert-butoxycarbonyl)amino]propanoate		C₁₈H₂₆N₂O₆	详情	详情
(V)	26615	ethyl (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propanoate		C₁₃H₁₈N₂O₄	详情	详情
(VI)	26616	N-(tert-butoxycarbonyl)-beta-alanine	3303-84-2	C₈H₁₅NO₄	详情	详情
(VII)	26617	ethyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-([3-[(tert-butoxycarbonyl)amino]propanoyl]amino)propanoate		C₂₁H₃₁N₃O₇	详情	详情
(VIII)	26618	ethyl (2S)-2-amino-3-([3-[(tert-butoxycarbonyl)amino]propanoyl]amino)propanoate		C₁₃H₂₅N₃O₅	详情	详情
(IX)	26619	4-ethylbenzenesulfonyl chloride	16712-69-9	C₈H₉ClO₂S	详情	详情
(X)	26620	ethyl (2S)-3-([3-[(tert-butoxycarbonyl)amino]propanoyl]amino)-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate		C₂₁H₃₃N₃O₇S	详情	详情
(XI)	26621	ethyl (2S)-3-[(3-aminopropanoyl)amino]-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate		C₁₆H₂₅N₃O₅S	详情	详情
(XII)	26622	4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoic acid		C₁₃H₁₆N₂O₄	详情	详情
(XIII)	26623	ethyl (2S)-3-[[3-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoyl]amino)propanoyl]amino]-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate		C₂₉H₃₉N₅O₈S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIII)

The deprotetion of (XIII) first with trifluoroacetic acid gives the ethyl ester (XIV), which is finally hydrolyzed with HCl in hot acetic acid.

参考文献中间体

合成目标

【1】 Ikeda, Y.; Ueki, Y.; Kishimoto, H.; Nishihara, T.; Kamikawa, Y. (Sumitomo Pharmaceuticals Co., Ltd.); 2,3-Diaminopropionic acid deriv.. US 5707994; US 6048854; WO 9511228 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIII)	26623	ethyl (2S)-3-[[3-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoyl]amino)propanoyl]amino]-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate		C₂₉H₃₉N₅O₈S	详情	详情
(XIV)	26624	ethyl (2S)-3-[[3-([4-[amino(imino)methyl]benzoyl]amino)propanoyl]amino]-2-[[(4-ethylphenyl)sulfonyl]amino]propanoate		C₂₄H₃₁N₅O₆S	详情	详情

Extended Information