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【结 构 式】 
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【分子编号】32772 【品名】(2S)-1-[(2-nitroanilino)carbonyl]-2-pyrrolidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C12H13N3O5 【 分 子 量 】279.25244 【元素组成】C 51.61% H 4.69% N 15.05% O 28.65% |
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：(V)The reaction of N-(tert-butoxycarbonyl)-L-(2-naphthyl)alanine (I) with N-methylbenzyamine (II) by means of isobutyl chloroformate and NMM in dichloromethane gives the corresponding amide (III), which is deprotected with HCl in dioxane yielding (IV) with a free amino group. Finally, this compound is condensed with 1-[N-(2-nitrophenyl)carbamoyl]-L-proline (V) by means of HOBT and DCC in THF. The intermediate 1-[N-(2-nitrophenyl)carbamoyl]-L-proline (V) has been obtained by reaction of L-proline (VI) with 2-nitrophenyl isocyanate (VII) by means of NMM in THF/water.
| 【1】 Prashad, M.; et al.; Process development of (2-nitrophenylcarbamoyl)-(S)-prolyl-(S)-3-(2-naphthyl)alanyl-N-benzyl-N-methylamide (SDZ NKT343). Org Process Res Dev 1999, 3, 6, 409. |
| 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) | 15061 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-naphthyl)propionic acid; N-T-BOC-L-3-(2-NAPHTHYL)ALANINE | 58438-04-3 | C18H21NO4 | 详情 | 详情 |
| (II) | 11969 | N-Methyl(phenyl)methanamine; N-Benzyl-N-methylamine; N-Methylbenzylamine | 103-67-3 | C8H11N | 详情 | 详情 |
| (III) | 15062 | tert-butyl N-[(1S)-2-[benzyl(methyl)amino]-1-(2-naphthylmethyl)-2-oxoethyl]carbamate | C26H30N2O3 | 详情 | 详情 | |
| (IV) | 15063 | (2S)-2-amino-N-benzyl-N-methyl-3-(2-naphthyl)propanamide | C21H22N2O | 详情 | 详情 | |
| (V) | 32772 | (2S)-1-[(2-nitroanilino)carbonyl]-2-pyrrolidinecarboxylic acid | C12H13N3O5 | 详情 | 详情 | |
| (VI) | 16731 | L-proline | 147-85-3 | C5H9NO2 | 详情 | 详情 |
| (VII) | 32771 | 1-isocyanato-2-nitrobenzene; 2-nitrophenyl isocyanate | 3320-86-3 | C7H4N2O3 | 详情 | 详情 |
Extended Information