반응 #640596

반응 방정식

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

acetyl chloride

→

title compound

수율 94.0%

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

수율 94.0%

용매

methanol

반응 조건

후처리

1. 1
   기타The residue obtained
2. 2
   기타after 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
   기타The organic layer was evaporated
6. 6
   건조dried (MgSO4)

실험 절차

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).

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