Reaction #640596

Reaction equation

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

acetyl chloride

→

title compound

Yield 94.0%

Methyl (4(S)-phenyloxazolidin-2-on-3-yl)acetate

Yield 94.0%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe residue obtained
2. 2
   Otherafter evaporation of the MeOH
3. 3
   workup.DISSOLUTIONwas redissolved in 30 mL of CH2Cl2
4. 4
   workup.ADDITIONtreated with 50 mL of saturated aqueous Na2CO3
5. 5
   OtherThe organic layer was evaporated
6. 6
   Dryingdried (MgSO4)

Procedure

A solution of (4(S)-phenyloxazolidin-2-on-3-yl)acetic acid (1 g, 4.52 mmol) (Evans in U.S. Pat. No. 4,665,171) in 20 mL of anhydrous methanol was treated hourly with 5 equivalents of acetyl chloride, for a total of 20 equivalents. The resulting solution was stirred overnight. The residue obtained after evaporation of the MeOH was redissolved in 30 mL of CH2Cl2 and treated with 50 mL of saturated aqueous Na2CO3. The organic layer was evaporated and dried (MgSO4) to yield the title compound as a colorless oil (1.001 g, 94%); 1H NMR (CDCl3) δ 3.37 (d, J=18.0 Hz, 1H), 3.69 (s, 3H), 4.13 (t, J=8.3 Hz, 1H), 4.28 (d, J=18.0 Hz, 1H), 4.69 (t, J=8.8 Hz, 1H), 5.04 (t, J=8.4 Hz, 1H), 7.26-7.29 (m, 2H), 7.36-7.42 (an, 3H).

Source