tert-butyl N-[2-(2-acetylhydrazinyl)-2-oxoethyl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 37.5 mL THF solution of tert-butyl[2-(2-acetylhydrazino)-2-oxoethyl]carbamate (496 mg, 2.15 mmol) was added Lawesson's reagent (900 mg, 2.23 mmol). The resulting reaction mixture was heated to reflux for 3 hr. The reaction was concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt & dichloromethane to give the title compound as white crystalline solid (391 mg). The resulting reaction mixture was heated to reflux for 3 hr The reaction was concentrated chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt & dichloromethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2 atmosphere, to a dichloromethane 10 mL solution of N-tert-butyloxycarbonyl-glycine (500 mg, 2.85 mmol) was added EEDQ (706 mg, 2.85 mmol). After stirring for 15 min, to it was added acethydrazide (260 mg, 3.51 mmol) and stirring continued at rt overnight. The precipitate was collected by suction filtration to give the title compound as white fluffy solid (496 mg). stirring continued at rt overnight The precipitate was collected by suction filtration