Water → 3-((4-(4-Fluorophenoxy)benzenesulfonyl)-(1-hydroxycarbamoylcyclopentyl)amino)propionic acid

HRID 1953214Notes

Reaction equation

HRID 1953214 reaction equation
C([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])[NH:14][OH:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)C.C1(C)C=CC=CC=1.O.[OH-].[Na+]>ClCCl>[F:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][C:23]2[CH:24]=[CH:25][C:20]([S:17]([N:7]([C:8]3([C:13](=[O:16])[NH:14][OH:15])[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:6][CH2:5][C:4]([OH:34])=[O:3])(=[O:19])=[O:18])=[CH:21][CH:22]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

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

Product 1

HCID 98691423-((4-(4-Fluorophenoxy)benzenesulfonyl)-(1-hydroxycarbamoylcyclopentyl)amino)propionic acidYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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 was stirred overnight. Filtration yielded 5.01 g of 3-[[4-(4-fluorophenoxy)benzenesulfonyl]-(1-hydroxy carbamoylcyclopentyl) amino]propionic acid as a white solid (71% yield from 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy) benzenesulfonyl]amino}cyclopentanecarboxylic acid).

Workup

  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. stirringwas stirred overnight
  12. filtrationFiltration

Sources & evidence

ORD record
ord-c94710e9e43f4c59a4ba41b67631f660
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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