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【结 构 式】 
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【分子编号】60839 【品名】benzyl (2S)-2-({[(1S)-1-benzyl-2-(tert-butoxy)-2-oxoethyl]amino}carbonyl)-2-methyl-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C27H34N2O5 【 分 子 量 】466.57744 【元素组成】C 69.51% H 7.34% N 6% O 17.15% |
合成路线1
该中间体在本合成路线中的序号：(V)N-Boc-L-Phenylalanine (I) is converted into the tert-butyl ester (II) upon treatment with tert-butyl trichloroacetimidate and boron trifluoride. Then, selective removal of the N-Boc group of (II) with HCl in EtOAc provides L-phenylalanine ester (III). Coupling of (III) with N-Cbz-2-methylproline (IV) furnishes dipeptide (V). After hydrogenolysis of the N-Cbz group of (V), the resultant amine (VI) is acylated by means of 3,5-dichlorobenzenesulfonyl chloride (VII), yielding sulfonamide (VIII). The tert-butyl ester group of (VIII) is finally cleaved by treatment with trifluoroacetic acid in CH2Cl2
| 【1】 Hagmann, W.K.; Durette, P.L.; Mumford, R.A.; Mills, S.G.; Kevin, N.J.; Schmidt, J.A.; MacCoss, M.; Van Riper, G.M. (Merck & Co., Inc.); Heterocyclic amide cpds. as cell adhesion inhibitors. EP 1001764; WO 9853814 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 61667 | tert-butyl 2,2,2-trichloroethanimidoate | C6H10Cl3NO | 详情 | 详情 | ||
| (I) | 22184 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionic acid | C14H19NO4 | 详情 | 详情 | |
| (II) | 60836 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate | C18H27NO4 | 详情 | 详情 | |
| (III) | 60837 | tert-butyl (2S)-2-amino-3-phenylpropanoate | C13H19NO2 | 详情 | 详情 | |
| (IV) | 60838 | (2S)-1-[(benzyloxy)carbonyl]-2-methyl-2-pyrrolidinecarboxylic acid | C14H17NO4 | 详情 | 详情 | |
| (V) | 60839 | benzyl (2S)-2-({[(1S)-1-benzyl-2-(tert-butoxy)-2-oxoethyl]amino}carbonyl)-2-methyl-1-pyrrolidinecarboxylate | C27H34N2O5 | 详情 | 详情 | |
| (VI) | 60840 | tert-butyl (2S)-2-({[(2S)-2-methylpyrrolidinyl]carbonyl}amino)-3-phenylpropanoate | C19H28N2O3 | 详情 | 详情 | |
| (VII) | 59023 | 3,5-dichlorobenzenesulfonyl chloride | C6H3Cl3O2S | 详情 | 详情 | |
| (VIII) | 60841 | tert-butyl (2S)-2-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]-2-methylpyrrolidinyl}carbonyl)amino]-3-phenylpropanoate | C25H30Cl2N2O5S | 详情 | 详情 |