4-Chloro-3-nitro-1,2-dihydropyridin-2-one → tert-butyl{(2R)-1-hydroxy-3-[(3-nitro-2-oxo-1,2-dihydropyridin-4-yl)sulfanyl]propan-2-yl}carbamate

Participants

Reaction Steps

A solution of 4-chloro-3-nitropyridin-2(1H)-one (1.61 g, 9.2 mmol) (or any other suitable activated aromatic compound) and TEA (2 ml, 14.4 mmol) in etanol (15 mL) stirred at 0° C., was treated with a solution of tert-butyl[(2R)-1-hydroxy-3-sulfanylpropan-2-yl]carbamate (42, 2.073 g, 10 mmol) in ethanol (10 mL+5 ml rinse) added from syringe. The final mixture was stirred at room temperature for 22 h (became a thick yellow suspension). Filtered, the cake washed with pentane and dried under vacuum, to afford the title compound (2.20 g, 69% yield) as a yellow solid, MS: m/z=368.1 (MNa+).

Provenance & Evidence