Water → Propionic Acid

HRID 1596008ノート

反応式

HRID 1596008 の反応式
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][N:7]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:8]1([C:13](=[O:16])NO)[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].C1(C)C=CC=CC=1.[OH2:42].[OH-].[Na+]>ClCCl>[C:4]([OH:34])(=[O:3])[CH2:5][CH3:6].[CH2:1]([O:3][C:4]([CH2:5][CH2:6][N:7]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:8]1([C:13]([OH:42])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:34])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 98057753-[[4-(4-Fluorophenoxy)benzenesulfonyl]-(1-hydroxycarbamoylcyclopentyl)amino]propionic acid ethyl ester

生成物 2

HCID 1032Propionic AcidHCID 110490941-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}-cyclopentanecarboxylic Acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 7.48 g (15.1 mmol) of 3-[[4-(4-fluorophenoxy)benzenesulfonyl]-(1-hydroxycarbamoylcyclopentyl)amino]propionic acid ethyl ester in dichloromethane was concentrated by rotary evaporation with the addition of 75 mL of toluene. This solution was treated with 75 mL of water, cooled to 0° C., and treated with 6.05 g (151 mmol, 10 equivalents) of sodium hydroxide pellets over 10 minutes with vigorous stirring. This mixture was stirred for 15 minutes at 0° C. and warmed to ambient temperature over one hour. The aqueous phase was separated, diluted with 7.5 mL of tetrahydrofuran, cooled to 0° C., and treated with 33 mL of 6N aqueous hydrochloric acid over 20 minutes. This mixture was stirred with 75 mL of ethyl acetate at 0° C. to ambient temperature, and the ethyl acetate phase was separated and washed with water. The ethyl acetate solution was slowly treated with 150 mL of hexanes at ambient temperature causing solids to precipitate, and stirred overnight. Filtration yielded 5.01 g of 3-[[4-(4-fluorophenoxy)benzenesulfonyl]-1-hydroxycarbamoylcyclopentyl)amino]propionic acid as a white solid (71% yield from 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid).

後処理

  1. temperaturewarmed to ambient temperature over one hour
  2. customThe aqueous phase was separated
  3. additiondiluted with 7.5 mL of tetrahydrofuran
  4. temperaturecooled to 0° C.
  5. additiontreated with 33 mL of 6N aqueous hydrochloric acid over 20 minutes
  6. stirringThis mixture was stirred with 75 mL of ethyl acetate at 0° C. to ambient temperature
  7. customthe ethyl acetate phase was separated
  8. washwashed with water
  9. additionThe ethyl acetate solution was slowly treated with 150 mL of hexanes at ambient temperature
  10. customto precipitate
  11. stirringstirred overnight
  12. filtrationFiltration

出典と根拠

ORDレコード
ord-138bfd89f3cb4cdb8a2cf667e0eff916
出典データセット
uspto-grants-2001_09
特許番号
US06288246B1

反応ノート

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