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【结 构 式】 
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【分子编号】38921 【品名】3-methyl-2-butanaminium (2S)-2-hydroxy-2-phenylethanoate 【CA登记号】 |
【 分 子 式 】C13H21NO3 【 分 子 量 】239.31468 【元素组成】C 65.25% H 8.84% N 5.85% O 20.06% |
合成路线1
该中间体在本合成路线中的序号：(V)The synthesis of the intermediates, the chiral amines (R)(-)-1,2-dimethylpropylamine (R)(-)-(I) and (S)(+)-1,2-dimethylpropylamine (S)(+)-(I) has been performed as follows: (R)(-)-1,2-Dimethylpropylamine (R)(-)-(I): The reaction of racemic 1,2-dimethylpropylamine (rac)(I) with 2(S)-(6-methoxynaphthalen-2-yl)propionic acid (S)(+)-(II) (S-naproxen) in ethanol gives the ammonium salt (III) as a diastereomeric mixture from which the (R,S)-diastereomer is obtained by successive crystallizations. Finally, this diastereomer is treated with NaOH in water to obtain the target (R)(-)-amine (R)(-)-(I). (S)(+)-1,2-Dimethylpropylamine (S)(+)-(I): The reaction of racemic 1,2-dimethylpropylamine (rac)-(I) with 2(S)-hydroxy-2-phenylacetic acid (S)(+)-(IV) (S-mandelic acid) in ethanol gives the ammonium salt (V) as a diastereomeric mixture from which the (S,S)-diastereomer is obtained by successive crystallizations. Finally, this diastereomer is treated with NaOH in water to obtain the target (S)(+)-amine (S)(+)-(I).
| 【1】 de Tullio, P.; Khelili, S.; Lebrun, P.; et al.; Preparation and pharmacological evaluation of the R- and S-enantiomers of 3-(2'-butylamino)-4H- and 3-(3'-methyl-2'-butylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide, two tissue selective ATP-sensitive potassium channel openers. Bioorg Med Chem 1999, 7, 8, 1513. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (S)(+)-(IV) | 12563 | (2S)-2-Hydroxy-2-phenylethanoic acid; S-(+)-Mandelic acid | 17199-29-0 | C8H8O3 | 详情 | 详情 |
| (S)(+)-(II) | 30839 | (2S)-2-(6-methoxy-2-naphthyl)propionic acid;(S)-naproxen;(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid | 22204-53-1 | C14H14O3 | 详情 | 详情 |
| rac-(I) | 38919 | 1,2-dimethylpropylamine; 3-methyl-2-butanamine | C5H13N | 详情 | 详情 | |
| (R)(-)-(I) | 38922 | (1R)-1,2-dimethylpropylamine; (2R)-3-methyl-2-butanamine | C5H13N | 详情 | 详情 | |
| (S)(+)-(I) | 38923 | (1S)-1,2-dimethylpropylamine; (2S)-3-methyl-2-butanamine | C5H13N | 详情 | 详情 | |
| (III) | 38920 | 3-methyl-2-butanaminium (2S)-2-(6-methoxy-2-naphthyl)propanoate | C19H27NO3 | 详情 | 详情 | |
| (V) | 38921 | 3-methyl-2-butanaminium (2S)-2-hydroxy-2-phenylethanoate | C13H21NO3 | 详情 | 详情 |