Sodium Hydroxide → 4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid

HRID 1929200ノート

反応式

HRID 1929200 の反応式
CC[O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[N:18]=[C:19]([CH3:22])[S:20][CH:21]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5].[OH-].[Na+]>C(O)C>[CH3:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[N:18]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 668421144-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

生成物 1

HCID 668416854-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

4-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (169) (1.75 g, 4.2 mmol) is dissolved in 20 ml of ethanol. After addition of a 0.5M aqueous sodium hydroxide solution (33.6 ml, 16.8 mmol) the solution is heated to 60° C. and stirred at this temperature for 18 h. Then the reaction mixture is evaporated and the residue is dissolved in ethyl acetate. AT 0° C. conc HCl is added until a pH of 1 is reached. The organic phase is washed with water and brine. The organic layers are dried over sodium sulphate, filtrated. The product crystallized upon evaporation and could be filtrated off.

後処理

  1. customThen the reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. additionAT 0° C. conc HCl is added until a pH of 1
  4. washThe organic phase is washed with water and brine
  5. dry with materialThe organic layers are dried over sodium sulphate
  6. filtrationfiltrated
  7. customThe product crystallized upon evaporation
  8. filtrationcould be filtrated off

出典と根拠

ORDレコード
ord-3927141ad5cc45ab83b9284a02fee496
出典データセット
uspto-grants-2012_05
特許番号
US08183366B2

反応ノート

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