Reaktion #640595

ord-3cbf28d41e1143919c8fbdf7395a26de

Reaktionsgleichung

O=C(O)CN1C(=O)OC[C@@H]1c1ccccc1
(4(S)-phenyloxazolidin-2-on-3-yl)acetic acid
O=C(Cl)C(=O)Cl
oxalyl chloride
CN(C)C=O
dimethylformamide
O=C(Cl)CN1C(=O)OC[C@@H]1c1ccccc1
title compound
O=C(Cl)CN1C(=O)OC[C@@H]1c1ccccc1
(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeresulting in vigorous gas evolution
  2. 2
    Einengenthe reaction mixture was concentrated under reduced pressure

Vorschrift

A solution of 1.0 equivalent of (4(S)-phenyloxazolidin-2-on-3-yl)acetic acid (Evans, U.S. Pat. No. 4,665,171) and 1.3 equivalent of oxalyl chloride in 200 mL dichloromethane was treated with a catalytic amount of anhydrous dimethylformamide (85 μL/milliequivalent of acetic acid derivative) resulting in vigorous gas evolution. After 45 minutes all gas evolution had ceased and the reaction mixture was concentrated under reduced pressure to provide the title compound as an off-white solid after drying for 2 h under vacuum.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08048874B2uspto-grants-2011_11