Di-tert-butyl oxalate → HCID 54691687, compound

Participants

Reaction Steps

To a solution of the title compound of Example B (29.37 g, 0.133 mol) and di-tert-butyl oxalate (26.90 g, 0.133 mol) in dry THF (350 ml) was added potassium tert-butoxide (29.84 g, 0.266 mol) and the resulting solution was heated under reflux for 24 h. The mixture was then cooled and the solvent removed in vacuo. The resulting solid was suspended in CH2Cl2 and 1N aqueous HCl was added. The resulting suspension was filtered and the organic filtrate was dried over MgSO4 and concentrated in vacuo. The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2 to give the title compound (19.06 g, 52%) as a solid. Anal calcd for C15H17NO4 : C, 65.44; H, 6.22; N, 5.09. Found: C, 65.05; H, 6.33; N, 4.86. MS M+1 calcd for C15H17NO4 276, found 276.

Provenance & Evidence