Dimethyl Sulfoxide → HCID 18470943, compound

Participants

Reaction Steps

Dry DMSO (3.0 ml, 43.54 mmol) in CH2Cl2 (6.9 ml) was added dropwise to a solution of oxalyl chloride (1.73 ml, 19.91 mmol) in CH2Cl2 (35 ml) at −60° C. under a nitrogen atmosphere. After stirring for 2 mins at −60° C. a solution of (RS)-benzyl-N-(2-hydroxy-3-phenylpropyl)carbamate (preparation 1) (5.18 g, 18.15 mmol) in CH2Cl2(17 ml) was added dropwise over 10 mins followed by triethylamine (17.63 ml, 90.74 mmol). The resultant mixture was allowed to warm to room temperature, whereupon water (100 ml) was added. The aqueous mixture was extracted with CH2Cl2 (3×100 ml) and the combined organic extracts washed with sat aq brine (2×250 ml) and dried over MgSO4. Filtration away from the drying agent followed by evaporation of the solvent gave the crude product which was purified by chromatography (SiO2; eluting with 40:60 hexane:ethyl acetate) to give the desired product (yellow crystalline solid, 4.41 g, 86%). 1H NMR (CDCl3) δ: 3.72 (s, 2H), 4.11 (d, 2H), 5.09 (s, 2H), 5.45 (s, br 1H), 7.20-7.37 (m, 10H). LRMS m/z=301.0 (M+18)+.

Provenance & Evidence