Triphenylphosphine → HCID 66847985, compound

Participants

Reaction Steps

A solution of racemic N-((1SR,2RS,4RS)-1-(3-bromo-4-fluorophenyl)-4-hydroxy-2-(hydroxymethyl)cyclopentylcarbamothioyl)benzamide (1.21 g, 2.02 mmol) and triphenylphosphine (0.690 mg, 2.63 mmol) in anhydrous THF (18 mL) is added to a separate solution of di-tert-butyl azodicarboxylate (0.606 g, 2.63 mmol) in THF (36 mL) at room temperature. The reaction mixture is stirred at room temperature for 1 hr and concentrated under reduced pressure to give a residue that is purified by silica gel chromatography eluting with a linear gradient of 0% to 40% ethyl acetate in dichloromethane over 15 minutes to give the title compound as racemic mixture (0.557 g, 61%). ES/MS m/e (79Br/81Br) 449, 451 (M+1).

Provenance & Evidence