Ammonia → Ipi-493

Participants

Reaction Steps

Geldanamycin (1.12 g, 2 mmol, 1 eq) was added to anhydrous dichloromethane (5 mL). NH3 in methanol was added to this solution (9 mL, 100 mmol, 50 eq) and was allowed to stir for 24 hours. The reaction solution was diluted with dichloromethane and extracted with water, followed by dilute HCl. The organic layer was collected washed with brine, dried over Na2SO4 and concentrated under reduced pressure to yield a purple solid. This solid was recrystalized twice from acetone/heptanes to yield 0.239 of 17-amino-17-demethoxygeldanamycin (17-AG).

Provenance & Evidence