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【结 构 式】 
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【分子编号】64381 【品名】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 【CA登记号】 |
【 分 子 式 】C31H43BrN6O9S 【 分 子 量 】755.68746 【元素组成】C 49.27% H 5.74% Br 10.57% N 11.12% O 19.05% S 4.24% |
合成路线1
该中间体在本合成路线中的序号：(XIV)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)
| 【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 | CAS号 | 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 |