Triethylamine → HCID 86731577, compound

Participants

Reaction Steps

To tert-butyl ethyl[(3aR,4aR,8aS,9R,9aR)-9-hydroxy-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d][1,3]thiazol-2-yl]carbamate (199.00 mg; 0.46 mmol; 1.00 eq.) in DCM (2.00 ml) was added methanesulfonyl chloride (0.05 ml; 0.68 mmol; 1.50 eq.) and N,N-diethylethanamine (0.09 ml; 0.68 mmol; 1.50 eq.). The reaction was stirred at room temperature for 2 h. The desired product was isolated by flash chromatography (KPNH, 20 to 75% EtOAc/Hex) to afford (3aR,4aR,8aR,9R,9aR)-2-[(tert-butoxycarbonyl)(ethyl)amino]-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d][1,3]thiazol-9-yl methanesulfonate (90 mg, 38%) as a white solid (once lyophilized).

Provenance & Evidence