Acetyl chloride → HCID 73891112, compound

Participants

Reaction Steps

Methyl 2-((4S,5S)-3-(4-cyanophenyl)-1-(4-((1-(5-ethoxy-2-fluorophenyl)piperidin-4-yl)oxy)phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-5-yl)acetate: 4-((4S,5S)-5-(Cyanomethyl)-1-(4-((1-(5-ethoxy-2-fluorophenyl)piperidin-4-yl)oxy)phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile (389 mg, 0.716 mmol) was dissolved in ˜2.5M HCl/MeOH, MeOAc, CH2Cl2 solution [36.6 mL, prepared by addition of AcCl (6.6 mL) to 3/2 CH2Cl2/MeOH (30.0 mL) at 0° C. and then stirring at rt for 30 min]. The resulting solution was stirred at rt for 6.5 h and then evaporated to a volume of about 5 mL. The oily remnant was stripped from MeOH (2×20 mL), taken up in EtOAc (100 mL) and, washed with 5% NaHCO3 (2×50 mL) and sat'd NaCl (40 mL). The organic layer was dried (Na2SO4) and concentrated. Purification via silica gel chromatography provided the desired (75 mg, 18% yield) as a yellow oil: LC-MS [M+H] 571.

Provenance & Evidence