O-Benzyl-N-[(benzyloxy)carbonyl]-L-threonine → HCID 18639971, compound

Participants

Reaction Steps

To a solution of O-benzyl-N-benzyloxycarbonyl-L-threonine (1.5 g), benzyl N-trifluoroacetyl-L-homoserinate (1.34 g) and 4-N,N-dimethylaminopyridine (48.8 mg) in methylene chloride (30 ml) was added N,N-diethylaminopropyl-N'-ethylcarbodiimide hydrochloride (840 mg) at 0° C. After stirring for an hour at room temperature, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate and washed successively with 0.1N hydrochloric acid, water, 10% aqueous sodium hydrogen carbonate, water and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was chromatographed on silica gel eluting successively with a 1:1 mixture of methylene chloride and hexane, methylene chloride and a 50:1 mixture of methylene chloride and acetone (50:1) to give benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-threonyl)-N-trifluoroacetyl-L-homoserinate (1.6 g).

Provenance & Evidence