Dimethyl Sulfoxide → HCID 86668650, compound

Participants

Reaction Conditions

Reaction Steps

To oxalyl chloride (1,842 ml, 3.68 mmol) in CH2Cl2 (12.300 ml) at −78° C. was added DMSO (0.523 ml, 7.37 mmol). The reaction mixture was stirred for 10 min and then {benzyl[(1R,2R)-2-hydroxycyclohexyl]amino}acetonitrile (2-1) (300 mg, 1.228 mmol) in 2 ml of CH2Cl2 was added. The reaction mixture was stirred at −78° C. for 1 hr before triethylamine (2.054 ml, 14.73 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min and then warm gradually to 0° C. After another 30 min the reaction was quenched by H2O. The reaction mixture was diluted with aqueous potassium carbonate (saturated, 20 mL) and extracted with dichloromethane (3×30 mL). The combined organic fractions were washed with brine (saturated, 30 mL), dried, filtered. The organic phase was concentrated and the residue was diluted with dry THF, filtered with 0.25 uM filter and concentrated to give the title compound. LRMS m/z (M+H) Calcd:243.1. found: 243.3.

Provenance & Evidence