Dicyclohexylcarbodiimide → (4S)-3-[({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetyl]-4-phenyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid (5.4 g, 16.5 mmol) was dissolved in dry CH2Cl2 (80 ml) and cooled to 0° C. N,N′-dicyclohexylcarbodiimide (DCC, 3.76 g; 18.2 mmol) in 20 ml of CH2Cl2 and 4-(dimethylamino)pyridine (DMAP, 4.04 g, 33.1 mmol) were added and the mixture was stirred at 0° C. for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (2.69 g, 16.5 mmol) was added and the mixture was stirred at room temperature for 17 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc 4:1 then 2:1). This afforded 5.69 g (73%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.3 (s, 3H), 2.8 (s, 2H), 3.4 (s, 4H), 3.8 (s, 2H), 3.8 (s, 3H), 4.3 (dd, 1H), 4.7 (t, 1H), 5.4 (dd, 1H), 6.9 (d, 2H), 7.3 (m, 7H).

Provenance & Evidence