Sulfuric Acid → HCID 15567308, compound

Participants

Reaction Steps

400 ml of isobutylene are added to a solution of 40 g (approx. 104 mmoles) of Z-D-Aad-OBzl in 400 ml of methylene chloride, followed, at -20°, by 4 ml of concentrated sulfuric acid. The mixture is allowed to stand in an autoclave for 3 days at room temperature. The batch is stirred with NaHCO3 solution in order to neutralize the sulfuric acid and the excess isobutylene is removed by means of a stream of nitrogen. The methylene chloride phase is extracted by shaking with water and is dried over Na2SO4 and concentrated. This leaves 46.3 g of an oil, which is chromatographed on 500 g of silica gel using a 9:1 mixture of methylene chloride and acetone. The eluate, which contains Z-Aad-(OBut)-OBzl, is concentrated. Yield: 42.35 g of a pale oil (92%).

Provenance & Evidence