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【结 构 式】 
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【分子编号】63391 【品名】3-cyclohexyl-N-(4-morpholinylcarbonyl)alanine 【CA登记号】 |
【 分 子 式 】C14H24N2O4 【 分 子 量 】284.35564 【元素组成】C 59.14% H 8.51% N 9.85% O 22.51% |
合成路线1
该中间体在本合成路线中的序号：(IV)Cyclohexylalanine benzyl ester (I) is acylated by 4-morpholinecarbonyl chloride (II) to furnish the urea derivative (III). The benzyl ester group of (III) is then removed by transfer hydrogenolysis, yielding N-(4-morpholinecarbonyl)-L-cyclohexylalanine (IV).
| 【1】 Frye, L.L.; Cywin, C.L.; Morwick, T.; Spero, D.M.; Thomson, D.; Ward, Y. (Boehringer Ingelheim Pharmaceuticals Inc.); Cpds. useful as reversible inhibitors of cathepsin S. JP 2002538151; US 6395897; WO 0051998 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 63389 | phenylmethyl 2-amino-3-cyclohexylpropanoate | C16H23NO2 | 详情 | 详情 | |
| (II) | 15847 | 4-morpholinecarbonyl chloride; Morpholine-4-carbonyl chloride | 15159-40-7 | C5H8ClNO2 | 详情 | 详情 |
| (III) | 63390 | phenylmethyl 3-cyclohexyl-2-[(4-morpholinylcarbonyl)amino]propanoate | C21H30N2O4 | 详情 | 详情 | |
| (IV) | 63391 | 3-cyclohexyl-N-(4-morpholinylcarbonyl)alanine | C14H24N2O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)N-Boc-O-Benzyl-L-serine (V) is treated with ammonium hydroxide and EDC/HOBt to afford the corresponding amide (VI). Subsequent acidic cleavage of the N-Boc group of (VI) provides O-benzyl-L-serinamide (VII). Then, coupling between cyclohexylalanine derivative (IV) and serinamide (VII) in the presence of EDC/HOBt furnishes the dipeptide derivative (VIII). Finally, dehydration of the terminal amide function of (VIII) by means of cyanuric chloride leads to the target nitrile.
| 【1】 Frye, L.L.; Cywin, C.L.; Morwick, T.; Spero, D.M.; Thomson, D.; Ward, Y. (Boehringer Ingelheim Pharmaceuticals Inc.); Cpds. useful as reversible inhibitors of cathepsin S. JP 2002538151; US 6395897; WO 0051998 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16886 | (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propionic acid; N-alpha-t-BOC-o-benzyl-L-serine | 23680-31-1 | C15H21NO5 | 详情 | 详情 |
| (IV) | 63391 | 3-cyclohexyl-N-(4-morpholinylcarbonyl)alanine | C14H24N2O4 | 详情 | 详情 | |
| (VI) | 63392 | 1,1-dimethylethyl 2-amino-2-oxo-1-{[(phenylmethyl)oxy]methyl}ethylcarbamate | C15H22N2O4 | 详情 | 详情 | |
| (VII) | 63393 | 2-amino-3-[(phenylmethyl)oxy]propanamide | C10H14N2O2 | 详情 | 详情 | |
| (VIII) | 63394 | N-[2-[(2-amino-2-oxo-1-{[(phenylmethyl)oxy]methyl}ethyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-morpholinecarboxamide | C24H36N4O5 | 详情 | 详情 |