Hydrochloric Acid → O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (19.4 g, 60% in mineral oil, 484.4 mmol) is washed with dry hexanes (2×30 mL) to remove the mineral oil and then suspended in anhydrous DMF (330 mL). To this suspension a solution of N-(t-butoxycarbonyl)-L-serine (45.2 g, 220.2 mmol) in DMF (110 mL) at 0° C. is added dropwise with vigorous stirring. The mixture is stirred for an additional 5 minutes at 0° C., and then at room temperature for 30 minutes. The solution is cooled back to 0° C., and a solution of allyl 3-iodomethylbenzoate (66.6 g, 220.2 mmol) in DMF (110 mL) is added dropwise over 15 minutes. The mixture is then warmed to room temperature for 30 minutes. The reaction mixture is poured into ice water (2.2 L) and acidified to pH 2 with 1 N HCl (270 mL). The mixture is extracted with ether (1×600 mL, then 3×300 mL) and the combined ether extracts are then washed with water (5×200 ml) and then dried (MgSO4) and evaporated in vacuo to yield O-[3-(allyloxycarbonyl)-benzyl]-N-(t-butoxycarbonyl)-L-serine as a yellowish oil.

Provenance & Evidence