Lithium Hydroxide → (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 2405906ノート

反応式

HRID 2405906 の反応式
[N:1]([CH2:4][CH2:5][C@@:6]([CH3:16])([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]([O:9]CC)=[O:8])=[N+:2]=[N-:3].[Li+].[OH-]>O>[N:1]([CH2:4][CH2:5][C@@:6]([CH3:16])([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 86710224ethyl (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoate

生成物 1

HCID 86710225(2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoic acid収率 35%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of ethyl (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoate (3.9 g, 15.6 mmol, 1 eq) in water (7.5 mL) was added LiOH (16 mmol). The mixture was allowed to stir at 80° C. for 16 h. The crude product was then purified by reverse phase chromatography on a 100 g C18 column eluting with a 0-20% MeOH/water gradient (containing 0.5% TFA) to give the desired product (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoic acid (1.2 g, 35% yield). LC-MS: M+H+222.1.

後処理

  1. customThe crude product was then purified by reverse phase chromatography on a 100 g C18 column
  2. washeluting with a 0-20% MeOH/water gradient (containing 0.5% TFA)

出典と根拠

ORDレコード
ord-4fe9e1b85e3f494bb1e7fa1b5159eba4
出典データセット
uspto-grants-2014_08
特許番号
US08809333B2

反応ノート

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