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

HRID 1953829
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1953829
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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 98691423-((4-(4-Fluorophenoxy)benzenesulfonyl)-(1-hydroxycarbamoylcyclopentyl)amino)propionic acidAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-df0cd55a8ef440e1b0d048baa785739d
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06118016

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