Reaction #640595

Reaction equation

(4(S)-phenyloxazolidin-2-on-3-yl)acetic acid

oxalyl chloride

dimethylformamide

→

title compound

(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherresulting in vigorous gas evolution
2. 2
   Concentrationthe reaction mixture was concentrated under reduced pressure

Procedure

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.

Source