Hydrochloric Acid → HCID 87952601, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium aluminum hydride (1.45 mL, 1.0 M in ether) was added in 3 portions over a period of 35 minutes to a solution of 3-(4-acetylamino-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (270 mg, 0.45 mmol) in dry ether (12 mL) and tetrahydrofuran (2 mL) at −65° C. under an atmosphere of dry nitrogen. The reaction mixture was stirred at −65° C. for an additional 10 minutes followed by the careful, dropwise addition of 0.3 N KHSO4 (10 mL) at −65° C. The reaction mixture was allowed to warm to room temperature and 0.1 N HCl (20 mL) was added. The organic layer was collected, dried (MgSO4) and evaporated to give the crude aldehyde (230 mg). Flash chromatography (silica, 2:1 ethyl acetate/hexane) provided pure 3-[4-acetylamino-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester (140 mg).

Provenance & Evidence