Methanol → (S)-2-[4-[[3,5-difluoro-4-[(S)-1-methoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid methyl ester

Participants

Reaction Steps

To a flask containing (S)-2-[4-[[3,5-difluoro-4-[(S)-1-carboxy-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid (560 mg, 0.59 mmol) was added methanol (50 mL) and TMSCI (398 mg, 460 mL, 3.66 mmol) and the reaction was stirred overnight. Reaction was diluted with EA (10 mL), DCM (140 mL) and was washed with aqueous NaHCO3 solution (water:saturated solution 50 mL:50 mL, 10 mL brine) and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated yielding the title compound as a white solid and used directly as is. ES(+)-LRMS m/e calcd. for C50H49F4N7O10 (M+H)+ 984, obsd 984.

Provenance & Evidence