Phthalimide → (+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl ester

Participants

Reaction Steps

Diethyl azodicarboxylate (5.7 ml, 36.2 mmol, abbreviated as DEAD hereinafter) was added dropwise to a mixture of (±)-N-(tert-butoxycarbonyl)homoserine allyl ester (7.79 g, 30.0 mmol), phthalimide (4.41 g, 30 mmol), triphenylphosphine (9.45 g, 36.0 mmol) and tetrahydrofuiran (75 ml) at room temperature with stirring. This mixture was stirred for 1 hour. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1 as the eluent to afford the desired compound (8.46 g, yield 73%) as a white powder.

Provenance & Evidence