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【结 构 式】 
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【分子编号】61217 【品名】CBZ-DL-Alanine; 2-[[(Benzyloxy)carbonyl]amino]propionic acid; N-((Phenylmethoxy)carbonyl)-DL-alanine; Carbobenzyloxy-DL-alanine 【CA登记号】4132-86-9 |
【 分 子 式 】C11H13NO4 【 分 子 量 】223.22856 【元素组成】C 59.19% H 5.87% N 6.27% O 28.67% |
合成路线1
该中间体在本合成路线中的序号：(B)Compound can be prepared in two different ways both starting from 2,6-xylidine (I): 1) By condensation of (I) with N-carbobenzoxyalanine (B) by means of dicyclohexylcarbodiimide in methylenechloride giving N-(carbobenzoxyalanyl)xylidine (II), which is then hydrogenated over Pd/C in ethanol - methylene chloride. 2) By condensation of (I) with 2-bromopropionyl bromide (A) by means of sodium acetate in acetic acid giving 2-bromo-2',6'-propionoxylidide (III), which is then treated with NH3 in alcohol water.
| 【1】 Boyes, R.N.; et al.; Propionamide derivative a method of making it and therapeutic compositions containing it. DE 2235745; FR 2147277; GB 1374367; NL 7210418 . |
| 【2】 Boyes, R.N.; et al.; Primary amino acylanilides methods of making the same and use as antiarrhythmic drugs. DE 2400540; ES 422085; FR 2213065; GB 1461602; JP 49116034 . |
| 【3】 Hillier, K.; Castaner, J.; Tocainide. Drugs Fut 1977, 2, 2, 141. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 13127 | 2-Bromopropionyl bromide; 2-Bromopropanoyl bromide | 563-76-8 | C3H4Br2O | 详情 | 详情 |
| (B) | 61217 | CBZ-DL-Alanine; 2-[[(Benzyloxy)carbonyl]amino]propionic acid; N-((Phenylmethoxy)carbonyl)-DL-alanine; Carbobenzyloxy-DL-alanine | 4132-86-9 | C11H13NO4 | 详情 | 详情 |
| (I) | 17527 | 2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine | 87-62-7 | C8H11N | 详情 | 详情 |
| (II) | 33595 | benzyl 2-(2,6-dimethylanilino)-1-methyl-2-oxoethylcarbamate | C19H22N2O3 | 详情 | 详情 | |
| (III) | 33594 | 2-bromo-N-(2,6-dimethylphenyl)propanamide | C11H14BrNO | 详情 | 详情 |