Hydrochloric Acid → HCID 69212227, compound

Participants

Reaction Steps

To a stirring solution of ethyl (2E)-3-{3-chloro-4-[((1R)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}-2-propenoate (54 mg, 0.10 mmol) in EtOAc (4 mL) under nitrogen at ambient temperature was added PtO2 (20 wt %, 11 mg) and the mixture stirred under an atmosphere of hydrogen for 5 h. The resulting mixture was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top, eluting with EtOAc. The filtrate was then reduced and purified further by SPE (silica, 5 g cartridge) eluting with cyclohexane:EtOAc (gradient 50:1 to 20:1) to give an inseparable mixture containing the desired material and some de -chlorinated compound (51 mg). This material was then dissolved in THF (2 mL) and MeOH (2 mL) at ambient temperature and treated with NaOH (2N, 2 mL). The resulting mixture was then stirred for 2 h and then left to stand overnight. HCl (2N, 2 mL) was then added and the mixture reduced under vacuum. The residue was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 20:1 to 0:1) to give a residue which was purified further by mass directed autoprep HPLC to give the title compound (30 mg).

Provenance & Evidence