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【结 构 式】 
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【分子编号】28238 【品名】benzyl (2S,3R)-3-amino-2-[(1S)-1-(ethoxycarbonyl)-2-methylpropyl]-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C19H28N2O4 【 分 子 量 】348.4424 【元素组成】C 65.49% H 8.1% N 8.04% O 18.37% |
合成路线1
该中间体在本合成路线中的序号：(XX)Alternative synthesis of intermediate (XI) of Scheme 25142902e: In an alternative procedure, (R)-asparagine (XII) was protected as the trifluoroacetamide (XIII) and then esterified by means of AcCl in MeOH yielding (XIV). Dehydration of the amide function of (XIV) employing tosyl chloride and pyridine produced nitrile (XV). The catalytic hydrogenation of (XV) with concomitant cyclization of the intermediate amine generated the chiral pyrrolidinone (XVI), which was protected with benzyl chloroformate and n-BuLi to give (XVII). This was converted to the intermediate (XI) by means of a sequence analogous to that for the racemic pyrrolidinone (IV).
| 【1】 Dowle, M.D.; Finch, H.; Harrison, L.A.; Inglis, G.G.A.; Johnson, M.R.; Macdonald, S.J.F.; Shah, P.; Smith, R.A. (Glaxo Wellcome plc); Pyrrolopyrrolone derivs. as inhibitors of neutrophil elastase. EP 0891362; JP 2000507950; US 5994344; WO 9736903 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 28227 | (Z)-1-ethoxy-3-methyl-1-butenyl triisopropylsilyl ether | C16H34O2Si | 详情 | 详情 | |
| (XI) | 28228 | benzyl (3aR,6S,6aS)-6-isopropyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate | C17H22N2O3 | 详情 | 详情 | |
| (XII) | 28237 | R-(-)-Asparagine; S-(-)-2-Aminosuccinamic acid; D-asparagine | 5794-13-8 | C4H8N2O3 | 详情 | 详情 |
| (XIII) | 28233 | (2R)-4-amino-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]butyric acid | C6H7F3N2O4 | 详情 | 详情 | |
| (XIV) | 28234 | methyl (2R)-4-amino-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]butanoate | C7H9F3N2O4 | 详情 | 详情 | |
| (XV) | 28235 | methyl (2R)-3-cyano-2-[(2,2,2-trifluoroacetyl)amino]propanoate | C7H7F3N2O3 | 详情 | 详情 | |
| (XVI) | 28236 | 2,2,2-trifluoro-N-[(3R)-2-oxopyrrolidinyl]acetamide | C6H7F3N2O2 | 详情 | 详情 | |
| (XVII) | 26700 | benzyl (3R)-2-oxo-3-[(2,2,2-trifluoroacetyl)amino]-1-pyrrolidinecarboxylate | C14H13F3N2O4 | 详情 | 详情 | |
| (XVIII) | 26702 | benzyl (3R)-2-ethoxy-3-[(2,2,2-trifluoroacetyl)amino]-1-pyrrolidinecarboxylate | C16H19F3N2O4 | 详情 | 详情 | |
| (XIX) | 26704 | benzyl (2S,3R)-2-[(1S)-1-(ethoxycarbonyl)-2-methylpropyl]-3-[(2,2,2-trifluoroacetyl)amino]-1-pyrrolidinecarboxylate | C21H27F3N2O5 | 详情 | 详情 | |
| (XX) | 28238 | benzyl (2S,3R)-3-amino-2-[(1S)-1-(ethoxycarbonyl)-2-methylpropyl]-1-pyrrolidinecarboxylate | C19H28N2O4 | 详情 | 详情 |