Ammonia → HCID 67462100, compound

Participants

Reaction Conditions

Reaction Steps

To mixture of 5-chloro-pyridine-2-carboxylic acid [4-fluoro-3-((1SR,7RS)-3-thioxo-5-oxa-2-aza-bicyclo[5.1.0]oct-1-yl)-phenyl]-amide (intermediate B14A) (142 mg, 0.36 mmol) and 7 N ammonia in methanol (3.1 ml) in methanol (15 ml) at 23° C. was added tert-butylhydroperoxide (70% in water, 0.50 ml, 3.62 mmol) and the mixture was stirred at 23° C. for 20 h. The reaction mixture was extracted with water and dichloromethane. The organic layer was washed with water and brine, the aqueous layers were reextracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a light yellow oil (180 mg, 132%), which was purified by silica gel column chromatography with dichloromethane to dichloromethane/methanol/ammonium hydroxide 65:10:1 to give the title compound as a white solid (10 mg, 7.4%). MS (ISP): m/z=375.3 [(M+H)+] and 377.3 [(M+2+H)+].

Provenance & Evidence