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【结 构 式】 
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【分子编号】54635 【品名】(4R,5S)-3-(2-bromopropanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one 【CA登记号】 |
【 分 子 式 】C13H14BrNO3 【 分 子 量 】312.1631 【元素组成】C 50.02% H 4.52% Br 25.6% N 4.49% O 15.38% |
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：(II)The enantioselective condensation of N-Boc-L-prolinal (I) with the chiral 2-bromopropionyloxazolidinone (II) by means of Co(PPh3)4 in THF gives the chiral beta-hydroxyamide (III), which is methylated by means of trimethyloxonium tetrafluoroborate in dichloromethane to yield the methyl ether (IV). Finally, elimination of the chiral auxiliary of (IV) by means of LiOH and H2O2 affords the target amino acid intermediate (V) (see scheme no. 14950701a , intermediate (XV)).
| 【1】 Pettit, G.R.; Grealish, M.P.; A cobalt-phosphine complex directed reformatsky approach to a stereospecific synthesis of the dolastatin 10 unit dolaproine (Dap). J Org Chem 2001, 66, 25, 8640. |
| 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) | 16734 | (2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid | C10H17NO4 | 详情 | 详情 | |
| (II) | 54635 | (4R,5S)-3-(2-bromopropanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one | C13H14BrNO3 | 详情 | 详情 | |
| (III) | 54614 | tert-butyl (2S)-2-{(1R,2R)-1-hydroxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}-1-pyrrolidinecarboxylate | C23H32N2O6 | 详情 | 详情 | |
| (IV) | 54636 | tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}-1-pyrrolidinecarboxylate | C24H34N2O6 | 详情 | 详情 | |
| (V) | 23520 | (2R,3R)-3-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-3-methoxy-2-methylpropionic acid | C14H25NO5 | 详情 | 详情 |
Extended Information