반응 #640597

반응 방정식

MeI

solution

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

lithium bis(trimethylsilyl)amide

→

title compound

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

용매

THF

THF

반응 조건

후처리

1. 1
   기타Upon complete conversion of the azetidinone, the reaction was quenched with saturated aqueous NH4Cl
2. 2
   기타partitioned between EtOAc and water
3. 3
   세척The organic layer was washed sequentially with saturated aqueous sodium bisulfite, and saturated aqueous NaCl
4. 4
   건조The resulting organic layer was dried (MgSO4)
5. 5
   기타evaporated

실험 절차

A solution of Example 2A (1 g, 4.25 mmol) in 10 mL of anhydrous THF at −78° C. was treated with 4.68 mL (4.68 mmol) of a 1 M solution of lithium bis(trimethylsilyl)amide in THF. The reaction mixture was stirred for 1 h. at about −70° C. before adding MeI (1.59 mL, 25.51 mmol). Upon complete conversion of the azetidinone, the reaction was quenched with saturated aqueous NH4Cl and partitioned between EtOAc and water. The organic layer was washed sequentially with saturated aqueous sodium bisulfite, and saturated aqueous NaCl. The resulting organic layer was dried (MgSO4) and evaporated to afford the title compound (a mixture of diasteromers) as a white solid (1.06 g, 93%); 1H NMR (CDCl3) δ 1.07/1.53 (d/d, J=7.5 Hz, 3H), 3.59/3.74 (s/s, 3H), 3.85/4.48 (q/q, J=7.5 Hz, 1H), 4.10-4.14 (m, 1H), 4.60-4.64/4.65-4.69 (m/m, 1H), 4.88-4.92/4.98-5.02 (m/m, 1H), 7.24-7.40 (m, 5H).

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