Lithium Hydroxide → 2-(4-(tert-Butoxycarbonyl(methyl)amino) phenyl)acetic acid

HRID 858056ノート

反応式

HRID 858056 の反応式
C[O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])=[CH:7][CH:6]=1.[OH-].[Li+]>CO>[C:16]([O:15][C:13]([N:11]([CH3:12])[C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:20])=[O:2])=[CH:10][CH:9]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 10636383Methyl 2-(4-(tert-butoxycarbonyl(methyl)amino)phenyl)acetate

生成物 1

HCID 107303972-(4-(tert-Butoxycarbonyl(methyl)amino) phenyl)acetic acid収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of [4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-acetic acid methyl ester (prepared according to the procedure of Hay et al. as described in J. Chem. Soc. Perkin Trans I. 1999, 19, 2759) (2.68 mmol) in methanol (10 mL) was added 1.0M aqueous lithium hydroxide solution (13.7 mL) and the mixture heated to 50° C. for 35 mins. The reaction mixture was cooled in an ice bath then washed with ether (25 mL), acidified with 3.0M aqueous hydrochloric acid to pH=4 while stirring and cooling in an ice bath. The precipitate was isolated by filtration, washed with water and dried in vacuo to give [4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-acetic acid as a colorless solid (70%).

後処理

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. washthen washed with ether (25 mL)
  3. temperaturecooling in an ice bath
  4. customThe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-3fa99353c6a047a9af3044ca72328568
出典データセット
uspto-grants-2006_12
特許番号
US07148229B2

反応ノート

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