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【结 构 式】 
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【分子编号】39528 【品名】N-benzoyl-3-[benzoyl(hydroxy)amino]alanine 【CA登记号】 |
【 分 子 式 】C17H16N2O5 【 分 子 量 】328.32452 【元素组成】C 62.19% H 4.91% N 8.53% O 24.37% |
合成路线1
该中间体在本合成路线中的序号：(X)The reaction of methyl 2-acetamido-3-chloropropionate (IX) with hydroxylamine followed by hydrolysis with concentrated HCl gives D,L-2-amino-3-hydroxyaminopropionic acid (VIII), which is benzoylated with benzoyl chloride in aqueous 10% NaOH yielding D,L-2-benzoylamino-3-(N-benzoyl-N-hydroxyamino)propionic acid (X). The resolution of (X) into optical isomers by treatment with cinchonine in ethanol, followed by treatment with 20% HCl at 100 C affords L-2-amino-3-hydroxyaminopropionic acid (L)-(VIII), which is nitrosated with NaNO2 and HCl. Racemic alanosine can be obtained by nitrosation of D,L-2-amino-3-hydroxyaminopropionic acid (VIII) obtained before.
| 【1】 Lancini, G.C.; et al.; Synthesis of homolog of the antibiotic alanosine. Farmaco 1969, 24, 2, 169-178. |
| 【2】 US 3823186 . |
| 【3】 Serradell, M.N.; Castañer, J.; Cabanillas, F.; Blancafort, P.; Alanosine. Drugs Fut 1979, 4, 7, 469. |
| 【4】 Eaton, C.N.; et al.; Improved synthesis of D,L-alanosine. J Med Chem 1973, 16, 3, 289-290. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (L)-(VIII) | 39525 | (2S)-2-amino-3-(hydroxyamino)propionic acid | C3H8N2O3 | 详情 | 详情 | |
| (VIII) | 39527 | 3-(hydroxyamino)alanine | C3H8N2O3 | 详情 | 详情 | |
| (IX) | 39526 | 2-acetamido-3-chloromethyl propionate; methyl 2-(acetamido)-3-chloropropanoate | 87333-22-0 | C6H10ClNO3 | 详情 | 详情 |
| (X) | 39528 | N-benzoyl-3-[benzoyl(hydroxy)amino]alanine | C17H16N2O5 | 详情 | 详情 |