(2R)-2-{[(4-bromobenzyl)sulfonyl]amino}-3-(tert-butoxy)propanoic acid -Drug Synthesis Database

【结构式】

【分子编号】64378

【品名】(2R)-2-{[(4-bromobenzyl)sulfonyl]amino}-3-(tert-butoxy)propanoic acid

【CA登记号】

【分子式】C₁₄H₂₀BrNO₅S

【分子量】394.28654

【元素组成】C 42.65% H 5.11% Br 20.27% N 3.55% O 20.29% S 8.13%

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：(X)

Acylation of O-t-butyl-D-serine methyl ester (VII) with sulfonyl chloride (VIII) yields sulfonamide (IX). After saponification of the methyl ester group of (IX) employing LiOH, the resultant carboxylic acid (X) is coupled to L-alanine t-butyl ester (XI) to furnish the sulfonyl dipeptide (XII). Acidic cleavage of the t-butyl ester group of (XII) gives rise to the carboxylic acid (XIII). This is then coupled to the benzylic amine (VI) to afford amide (XIV). Finally, the N-Boc protecting groups of (XIV) are removed by treatment with trifluoroacetic acid in CH2Cl2. (1,2)

参考文献中间体

合成目标

【1】 Tamiz, A.P.; Weinhouse, M.I.; Ahn, J.S.; Alfaro-Lopez, J.; Gaudette, J.; Meneses, J.K.; Roberts, C.; Madison, E.L.; Semple, J.E.; Levy, O.E..; Synthesis and biological activity of non-transition state urokinase inhibitors. 28th Natl Med Chem Symp (June 8 2002, San Diego) 2002, Abst 59.
【2】 Semple, J.E.; Levy, O.E.; Tamiz, A.P.; Madison, E.L.; Weinhouse, M.I. (Corvas International, Inc.); Non-covalent inhibitors of urokinase and blood vessel formation. EP 1182207; WO 0214349 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	64374	tert-butyl {[4-(aminomethyl)phenyl]imino}[(tert-butoxycarbonyl)amino]methylcarbamate	C₁₈H₂₈N₄O₄	详情	详情
(VII)	64375	methyl (2R)-2-amino-3-(tert-butoxy)propanoate	C₈H₁₇NO₃	详情	详情
(VIII)	64376	(4-bromophenyl)methanesulfonyl chloride	C₇H₆BrClO₂S	详情	详情
(IX)	64377	methyl (2R)-2-{[(4-bromobenzyl)sulfonyl]amino}-3-(tert-butoxy)propanoate	C₁₅H₂₂BrNO₅S	详情	详情
(X)	64378	(2R)-2-{[(4-bromobenzyl)sulfonyl]amino}-3-(tert-butoxy)propanoic acid	C₁₄H₂₀BrNO₅S	详情	详情
(XI)	29385	tert-butyl (2S)-2-aminopropanoate	C₇H₁₅NO₂	详情	详情
(XII)	64379	tert-butyl (2S)-2-{[(2R)-2-{[(4-bromobenzyl)sulfonyl]amino}-3-(tert-butoxy)propanoyl]amino}propanoate	C₂₁H₃₃BrN₂O₆S	详情	详情
(XIII)	64380	(2S)-2-[((2R)-2-{[(4-bromobenzyl)sulfonyl]amino}-3-hydroxypropanoyl)amino]propanoic acid	C₁₃H₁₇BrN₂O₆S	详情	详情
(XIV)	64381	tert-butyl ({4-[(4S,7R)-10-(4-bromophenyl)-7-(hydroxymethyl)-4-methyl-3,6,9,9-tetraoxo-9lambda~6~-thia-2,5,8-triazadec-1-yl]phenyl}imino)[(tert-butoxycarbonyl)amino]methylcarbamate	C₃₁H₄₃BrN₆O₉S	详情	详情

Extended Information