Phosgene → HCID 118098732, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 16K (0.144 g, 0.175 mmol) in acetonitrile (5 mL) and dichloromethane (2.5 mL) at 0° C. was added phosgene solution (20% in toluene, 0.101 mL, 0.192 mmol) dropwise. The mixture was stirred at 0° C. for 30 min. Extra phosgene was removed by bubbling Ar for 20 min. The resulting solution was added dropwise via syringe pump into a solution of TEA (0.195 mL, 1.398 mmol) in dichloromethane (60 mL) at rt over 3.0 h. The reaction mixture was stirred at rt over night. The solvent was removed and the crude product was purified by flash chromatography (0-80% ethyl acetate/hexanes). The desired fractions were collected, concentrated to give a mixture of diastereoisomers (0.12 g, 0.141 mmol, 81% yield). The diastereoisomers were separated using a prep chiral HPLC equipped with a Whelko-01 column to give 16L (34 mg, 48% yield). MS (ESI) (m/z): 850.0 (M+H)+.

Provenance & Evidence