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【结 构 式】

【分子编号】26613

【品名】(2S)-2-[[(benzyloxy)carbonyl]amino]-3-[(tert-butoxycarbonyl)amino]propionic acid

【CA登记号】

【 分 子 式 】C16H22N2O6

【 分 子 量 】338.36056

【元素组成】C 56.8% H 6.55% N 8.28% O 28.37%

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:(III)

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).

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
Extended Information