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【结 构 式】

【分子编号】32578

【品名】methyl (2S)-2-amino-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate

【CA登记号】

【 分 子 式 】C17H16Cl2N2O3

【 分 子 量 】367.23112

【元素组成】C 55.6% H 4.39% Cl 19.31% N 7.63% O 13.07%

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)

Fischer esterification of L-4-nitrophenylalanine (V) afforded nitrophenylalanine methyl ester (VI), which was then protected as the tert-butyl carbamate (VII) using (Boc)2O. Reduction of the nitro group of (VII) by catalytic hydrogenation gave aniline (VIII). Subsequent coupling of (VIII) with 2,6-dichlorobenzoyl chloride (IX) generated amide (X). Deprotection of the Boc group of (X) using HCl in dioxan provided aminoester (XI), which was coupled with camphoric acid derivative (IV) in the presence of benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluoro-phosphate (BOP) to yield amide (XII). Deprotection of the tert-butyl ester group of (XII) by means of trifluoroacetic acid gave acid (XIII). Finally, the methyl ester group of (XIII) was hydrolyzed with LiOH to furnish the title compound.

1 Rishton, G.; Chrusciel, R.A.; Yamagishi, M.; Polinsky, A.; Thomas, E.W.; Lobl, T.J.; Tanis, S.P.; Teegarden, B.; Fisher, J.F. (Pharmacia Corp.; Tanabe Seiyaku Co., Ltd.); Inhibitors of alpha4beta1 mediated cell adhesion. EP 0991619; WO 9858902 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 32572 (1S,3R)-3-(tert-butoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid C14H24O4 详情 详情
(V) 15341 (2S)-2-amino-3-(4-nitrophenyl)propionic acid; 4-nitro-L-phenylalanine 949-99-5 C9H10N2O4 详情 详情
(VI) 15342 methyl (2S)-2-amino-3-(4-nitrophenyl)propanoate C10H12N2O4 详情 详情
(VII) 32574 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-nitrophenyl)propanoate C15H20N2O6 详情 详情
(VIII) 32575 methyl (2S)-3-(4-aminophenyl)-2-[(tert-butoxycarbonyl)amino]propanoate C15H22N2O4 详情 详情
(IX) 25087 2,6-dichlorobenzoyl chloride 4659-45-4 C7H3Cl3O 详情 详情
(X) 32576 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate C22H24Cl2N2O5 详情 详情
(XI) 32578 methyl (2S)-2-amino-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate C17H16Cl2N2O3 详情 详情
(XII) 32573 tert-butyl (1R,3S)-3-[[((1S)-1-[4-[(2,6-dichlorobenzoyl)amino]benzyl]-2-methoxy-2-oxoethyl)amino]carbonyl]-1,2,2-trimethylcyclopentanecarboxylate C31H38Cl2N2O6 详情 详情
(XIII) 32577 (1R,3S)-3-[[((1S)-1-[4-[(2,6-dichlorobenzoyl)amino]benzyl]-2-methoxy-2-oxoethyl)amino]carbonyl]-1,2,2-trimethylcyclopentanecarboxylic acid C27H30Cl2N2O6 详情 详情
Extended Information