Reaktion #954605

ord-de03737a281c42dd882d5acde6f2f4c8

Reaktionsgleichung

CC(=O)OC(C)=O
acetic anhydride
CC1(C)SC(c2ccc(Cl)cc2)N[C@H]1C(=O)O
2-(4-chlorophenyl)-5,5-dimethylthiazolidine-4(S)-carboxylic acid
→
CC(=O)N1[C@@H](C(=O)O)C(C)(C)S[C@H]1c1ccc(Cl)cc1
title compound
CC(=O)N1[C@@H](C(=O)O)C(C)(C)S[C@H]1c1ccc(Cl)cc1
3-Acetyl-2(S)-(4-chlorophenyl)-5,5-dimethylthiazolidine-4(S)-carboxylic acid

Edukte

CC(=O)OC(C)=O
acetic anhydride
CC1(C)SC(c2ccc(Cl)cc2)N[C@H]1C(=O)O
2-(4-chlorophenyl)-5,5-dimethylthiazolidine-4(S)-carboxylic acid

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeA complete solution is obtained
  2. 2
    TemperaturOn cooling
  3. 3
    Sonstigethe product precipitates

Vorschrift

5.6 ml of acetic anhydride are given to a suspension containing 2.71 g (10 mmoles) of 2-(4-chlorophenyl)-5,5-dimethylthiazolidine-4(S)-carboxylic acid in 5.6 ml of hot water and the mixture is kept at 100° C. for 8 minutes. A complete solution is obtained. On cooling, the product precipitates to give the title compound in a yield of 2.39 g (76.1%) which is recrystallized from ethanol by adding water, m.p.: 203°-205° C., [α]D22 =+111.5° (c=1.44, dimethylsulphoxide).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04775675uspto-grants-1988_10