|
【结 构 式】 
|
【分子编号】42785 【品名】(2S)-2-hydroxy-4-methylpentanoic acid 【CA登记号】13748-90-8 |
【 分 子 式 】C6H12O3 【 分 子 量 】132.15948 【元素组成】C 54.53% H 9.15% O 36.32% |
合成路线1
该中间体在本合成路线中的序号：(IV)Synthesis of intermediate 2(S)-[3-(tert-butoxycarbonylamino)-2,2-dimethylpropionyloxy]-4-methylpentanoic acid (VIII): The reaction of 3-amino-2,2-dimethyl-1-propanol (I) with Boc2 and Et3N in methanol gives the carbamate (II), which is oxidized with NaIO4 in CCl4/acetonitrile/water yielding 3-(tert-butoxycarbonylamino)-2,2-dimethylpropionic acid (III). The esterification of 2(S)-hydroxy-4-methylpentanoic acid (IV) with allyl bromide (V), NaHCO3 and tetrabutylammonium chloride in dichloromethane/water affords the corresponding allyl ester (VI). The esterification of hydroxyester (VI) with amino acid (II) by means of DCC and DMAP in dichloromethane provides the corresponding diester (VII), which is finally treated with Pd(PPh3)4 and morpholine in THF to furnish the intermediate 2(S)-[3-(tert-butoxycarbonylamino)-2,2-dimethylpropionyloxy]-4-methylpentanoic acid (VIII).
| 【1】 WO 9640184 . |
| 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) | 42783 | 3-amino-2,2-dimethyl-1-propanol | 26734-09-8 | C5H13NO | 详情 | 详情 |
| (II) | 42784 | tert-butyl 3-hydroxy-2,2-dimethylpropylcarbamate | C10H21NO3 | 详情 | 详情 | |
| (III) | 18901 | N-(tert-butoxycarbonyl)-2,2-dimethyl-beta-alanine | C10H19NO4 | 详情 | 详情 | |
| (IV) | 42785 | (2S)-2-hydroxy-4-methylpentanoic acid | 13748-90-8 | C6H12O3 | 详情 | 详情 |
| (V) | 11720 | 4-Bromo-1-butene | 5162-44-7 | C4H7Br | 详情 | 详情 |
| (VI) | 18902 | allyl (2S)-2-hydroxy-4-methylpentanoate | C9H16O3 | 详情 | 详情 | |
| (VII) | 18903 | allyl (2S)-2-([3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl]oxy)-4-methylpentanoate | C19H33NO6 | 详情 | 详情 | |
| (VIII) | 18904 | (2S)-2-([3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl]oxy)-4-methylpentanoic acid | C16H29NO6 | 详情 | 详情 |