Allyl bromide → (S)-3-(Allyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of Boc-Ser-OH (21.5 g, 0.105 mol) in DMF at 0° C. was added sodium hydride (8.4 g, 0.21 mol). The reaction mixture was stirred at 0° C. for 15 mins, and then allyl bromide (13.3 g, 0.105 mol) was added. The mixture was stirred at 40° C. overnight. After TLC showed the reaction was completed, the mixture was quenched with aqueous NH4Cl solution and concentrated in vacuum. The residue was diluted with water, and sequentially washed with hexane and ether. The organic layers were discarded, and the aqueous layer was carefully adjusted to pH=3 with 1 N HCl. The acidic aqueous solution was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated in vacuum to give Boc-Ser(O-allyl)-OH (14.0 g, 54.4%).

Provenance & Evidence