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【结 构 式】

【分子编号】38474

【品名】ethyl (3S)-3-(1,3-benzodioxol-5-yl)-3-([[((1S)-1-[[bis(2-thienylmethyl)amino]carbonyl]pentyl)amino]carbonyl]amino)propanoate

【CA登记号】

【 分 子 式 】C29H35N3O6S2

【 分 子 量 】585.74552

【元素组成】C 59.47% H 6.02% N 7.17% O 16.39% S 10.95%

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:(XIV)

Treatment of 3,4-(methylenedioxy)cinnamic (VII) with SOCl2 and then with EtOH provided ethyl ester (VIII). Subsequent conjugate addition of the chiral amine (IX) to ester (VIII) in the presence of BuLi gave amino ester (X). Cleavage of benzyl and alpha-methylbenzyl protecting groups of (X) was then achieved by catalytic hydrogenolysis over Pd/C. The resulting primary amine (XI) was acylated with 4-nitrophenyl chloroformate (XII) to produce carbamate (XIII), which was condensed with amine (VI) to generate urea (XIV). Finally, basic hydrolysis of the ethyl ester of (XIV) furnished the title carboxylic acid.

1 Scott, I.L.; et al.; Novel N,N-disubstituted amides that are highly potent VLA-4 antagonists. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 284.
2 Raju, B.G.; Scott, I.L.; Biediger, R.J.; Market, R.V.; Grabbe, V.O.; Kassir, J.M.; Kogan, T.P.; Lin, S. (Texas Biotechnology Corp.); N,N-Disubstd. amides that inhibit the binding of integrins to their receptors. US 6096773; WO 9952493; WO 9952898 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 38468 (2S)-2-amino-N,N-bis(2-thienylmethyl)hexanamide C16H22N2OS2 详情 详情
(VII) 11634 (E)-3-(1,3-Benzodioxol-5-yl)-2-propenoic acid; 3,4-(Methylenedioxy)cinnamic acid 2373-80-0 C10H8O4 详情 详情
(VIII) 38469 ethyl (E)-3-(1,3-benzodioxol-5-yl)-2-propenoate C12H12O4 详情 详情
(IX) 38470 (1S)-N-benzyl-1-phenyl-1-ethanamine; N-benzyl-N-[(1S)-1-phenylethyl]amine 38235-77-7 C15H17N 详情 详情
(X) 38471 ethyl (3S)-3-(1,3-benzodioxol-5-yl)-3-[benzyl[(1S)-1-phenylethyl]amino]propanoate C27H29NO4 详情 详情
(XI) 38472 ethyl (3S)-3-amino-3-(1,3-benzodioxol-5-yl)propanoate C12H15NO4 详情 详情
(XII) 16605 4-Nitrophenyl chloroformate; 1-[(Chlorocarbonyl)oxy]-4-nitrobenzene 7693-46-1 C7H4ClNO4 详情 详情
(XIII) 38473 ethyl (3S)-3-(1,3-benzodioxol-5-yl)-3-[[(4-nitrophenoxy)carbonyl]amino]propanoate C19H18N2O8 详情 详情
(XIV) 38474 ethyl (3S)-3-(1,3-benzodioxol-5-yl)-3-([[((1S)-1-[[bis(2-thienylmethyl)amino]carbonyl]pentyl)amino]carbonyl]amino)propanoate C29H35N3O6S2 详情 详情
Extended Information