Dicyclohexylcarbodiimide → (4S)-3-[({[2-(4-Chlorophenyl)-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-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid (2.00 g, 6.05 mmol) was dissolved in dry CH2Cl2 (45 ml) and cooled to 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 1.43 g, 6.93 mmol) and 4-(dimethylamino)pyridine (DMAP, 1.70 g, 10.4 mmol) were added and the mixture was stirred at 0° C. for 20 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1.40 g, 11.5 mmol) was added and the mixture was stirred at room temperature for 70 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (20%-30% EtOAc in hexane). This afforded 1.27 g (44%) of the title compound as a white solid. 1H-NMR (CDCl3, 300 MHz): δ 0.62 (s, 3H), 1.34 (s, 3H), 2.78 (s, 2H), 3.42 (s, 4H), 3.85 (s, 2H), 4.27-4.33 (dd, 1H), 4.69-4.78 (t, 1H), 5.34-5.42 (dd, 1H), 7.29-7.38 (m, 9H).

Provenance & Evidence