HCID 78035251, compound → HCID 71486743, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (1SR,7SR)-1-(5-(5-chloropicolinamido)-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (intermediate rac-A9a) (29 mg; 0.06 mmol) was dissolved in dichloromethane (3 ml) and at 23° C. trifluoroacetic acid (TFA) (0.8 ml) was added. The yellow solution was stirred for 2 hours at 23° C. The reaction mixture was extracted with sat NaHCO3 solution 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 Na2SO4, filtered and evaporated to give a light yellow oil which was chromatographed on 10 g SiO2—NH2 with dichloromethane+dichloromethane/methanol 19:1 to give the 5-chloro-pyridine-2-carboxylic acid [3-((1SR,7SR)-3-amino-4-thia-2-aza-bicyclo[5.1.0]oct-2-en-1-yl)-4-fluoro-phenyl]-amide (13.34 mg; 58%) as an off white solid. MS (ISP): m/z=391.0 [(M+H)+] and 393.1 [(M+2+H)+].

Provenance & Evidence