Triphenylphosphine → (3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidine

Participants

Reaction Steps

A solution of 12.67 g of N-benzyloxy-t-butoxycarbonyl-threonine amide, 11.5 g of triphenylphosphine, and 6.23 ml of diethylazodicarboxylate in 380 ml of tetrahydrofuran was stirred under nitrogen for about 16 hours. The solution was evaporated and chromatographed on a 900 g silica gel column. Elution with chloroform-ethyl acetate (3:1) gave 13.69 g of compound that crystallized from ether-hexane to yield 9.18 g of the title compound.

Provenance & Evidence