Toluene → HCID 178432669, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (-78° C.) solution of 2,4-dimethyl-8-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (1.57 g, 2.41 mmol) in THF (5 mL) was added 0.5M potassium hexamethyldisilazide in toluene (5.5 mL, 2.75 mmol). After 45 min, a solution of (+)-camphorsulfonyloxaziridine in THF (5 mL) was added. The mixture was allowed to warm to 5° C. over 5 h. Water (2 mL) and CF3CO2H (2 mL) were added and stirring was continued for 1 h. 1N NaOH (30 mL) was added and the mixture was extracted with EtOAc (discarded). The aqueous phase was acidified to pH 4 with 1N HCl and extracted with CHCl3. The extracts were dried MgSO4) and concentrated. Purification by flash chromatography (5-10% MeOH/CHCl3) gave 377 mg of a yellow oil. Crystallization from acetone yielded 234 mg (23%) of product as an off-white solid, mp 154°-156° C.

Provenance & Evidence