Phosgene → HCID 131733873, compound

Participants

Reaction Steps

Phosgene (201 mg, 0.406 mmol) was added dropwise to a solution of 22D (297 mg, 0.369 mmol) in acetonitrile (4 mL)/CH2Cl2 (4 mL) at 0° C. The bath was removed and the mixture was stirred at rt for 30 min. Ar was bubbled though the solution (10 min) to remove excess phosgene. The resulting solution was added to a solution of TEA (0.257 mL, 1.847 mmol) in CH2Cl2 (40 mL) at 40° C. over 5 h via a syringe pump. The reaction was stirred at rt overnight, quenched with H2O (1 mL) and MeOH (5 mL) and then concentrated. The crude product was purified by flash chromatography to give a mixture of diastereoisomers. The diastereomers were separated by a prep chiral HPLC (R,R-Whelk-O column 21.1×250 mm) to give 22E (75 mg, 0.090 mmol, 24.46% yield). MS (ESI) m/z: 830.8 (M+H)+.

Provenance & Evidence