(5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)(tert-butoxycarbonyl)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate → (5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1 (2H)-carboxylate

Participants

Reaction Steps

To a solution of (5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)(tert-butoxycarbonyl)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 161, 1.19 g, 1.67 mmol) in DCM (20 mL) at room temperature was added zinc bromide (1.502 g, 6.67 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate and. The aqueous wash was extracted three to four times more with DCM. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound (0.970 g, 95%) as an off white foam.

Provenance & Evidence