HCID 18689654, compound → HCID 54214489, compound

Participants

Reaction Conditions

Reaction Steps

7-Benzhydryloxy-1-(4-methoxybenzenesulfonyl)-2,5,5a,8a-tetrahydro-1H-pyrrolo[3,4-b]azepine-6,8-dione (100 mg, 0.19 mmol) was dissolved in THF (2 mL) and cooled to -78° C. This solution was treated dropwise with a 3 M solution of phenyl magnesium bromide in diethyl ether and then warmed to ambient temperature. The reaction mixture was stirred another 2.5 hrs at room temperature, cooled to 0° C., and quenched with saturated aqueous NH4Cl (2 mL). This mixture was then diluted with H2O and diethyl ether and the layers were separated. The organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 5 to 10% ethyl acetate in toluene) to give 3-benzoyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid benzhydryloxy-amide; MS: (M+H)+ 596.9, (M+NH4)+ 614.2.

Provenance & Evidence