Triphenylphosphine → HCID 59497418, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-7-hydroxymethyl-2-oxo-benzooxazole-3-carboxylic acid tert-butyl ester 600 mg (2 mmol) is dissolved in tetrahydrofuran 1.5 mL and then 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester is added (608 mg (2.2 mmol). The reaction is cooled to 0° C. and then triphenylphosphine (630 mg, 2.4 mmol) is added followed by the drop wise addition of diisopropyl azodicarboxylate (465 μL, 2.40 mmol). The reaction is stirred for 15 minutes at 0° C. and then the solvents evaporated in vacuo. The compound is purified on silica with dichloromethane methanol as the eluent. This crude material is then taken up in dichloromethane (1.5 mL) and trifluoroacetic acid (500 uL) is added drop wise to the reaction. The reaction is stirred at room temperature and monitored by LC/MS. Upon completion the reaction is evaporated in vacuo and purified by preparative reverse phase LC to give the title compound 33 mg (0.07 mmol, 3.6%). LCMS (ESMS): m/z 444.9 (M+H+).

Provenance & Evidence