Phosgene → HCID 118098763, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 26A (80 mg, 0.099 mmol) in acetonitrile (6 mL) and dichloromethane (3 mL) at 0° C., was added phosgene solution (20% in toluene, 0.063 mL, 0.119 mmol) dropwise. The mixture was stirred at 0° C. for 40 min, then at rt for 30 min. Extra phosgene was removed by bubbling Ar though the reaction mixture (30 min). The mixture was added dropwise via syringe pump into a solution of TEA (0.111 mL, 0.794 mmol) in dichloromethane (40 ml) at rt over 3.0 h. The solution was stirred at rt overnight, quenched with 0.5 N HCl, extracted with CH2Cl2. The organic layer was washed with water and dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography (30-100% EtOAc/hexanes) to give a mixture of diastereoisomers (70 mg, 0.084 mmol, 85% yield). The diastereomers were separated by a prep chiral HPLC (R,R-Whelk-O column 21.1×250 mm) to give 26B (30 mg, 0.036 mmol, 42.9% yield). MS (ESI) m/z: [M+1]+. 19F NMR (376 MHz, CDCl3) d ppm −128.71 (s, 1F).

Provenance & Evidence