Dicyclohexylcarbodiimide → (4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

(4-Methoxy-benzylsulfanyl)-acetic acid (1.3 g, 6.1 mmol) was dissolved in dry DCM (40 ml) and cooled to 0° C. N,N′-dicyclohexylcarbodiimide (6.1 g, 6.1 mmol) and DMAP (1.6 g, 12.9 mmol) were added and the mixture was stirred for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1.0 g, 6.1 mol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was filtrated, concentrated under reduced pressure and purified by flash-chromatography (Hex:EtOAc 8:2 then 1:1). This afforded 1.7 g (77%) of the title compound as a white solid. NMR (200 MHz): 3.46-3.59 (m, 3H), 3.74-3.76 (m, 4H), 4.23-4.28 (m, 1H), 4.68 (t, 1H), 5.38-5-42 (m, 1H), 6.78 (d, 2H), 7.14 (d, 2H), 7.32-7.40 (m, 5H).

Provenance & Evidence