Benzyl chloroformate → (S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-benzyloxycarbonyl-4-azaoctanedioic acid

Participants

Reaction Conditions

Reaction Steps

1M NaHCO3 (5.9 ml, 5.92 mmol ) and benzyloxycarbonyl chloride (0.5 g, 0.42 ml, 2.96 mmol) were added to a solution of (S,S)-2,7-bis (tert-butyloxycarbonylamino)-4-azaoctanedioic acid (0.6 g, 1.48 mmol) in dioxane (40 ml ) and H2O (30 ml ) at 0° C. The mixture was stirred at 0° C. for 3 hours, at ambient temperature for 6 hours, evaporated, the residue triturated with chloroform (5 ml) and acetic acid to pH 5. The chloroform solution was evaporated and the product isolated after chromatography on silica gel (CHCl3 : MeOH 4:1).

Provenance & Evidence