Hydrochloric Acid → 1-((3-Fluoro-4-(5-(2-phenyloxetan-2-yl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of trimethylsulfoxonium iodide (230 mg, 1047 μmol) and potassium t-butoxide (1.0M in t-BuOH) (1.047 ml, 1.047 mmol) in t-BuOH (1.0 mL) was stirred at 50° C. for 30 min. 1-((4-(5-Benzoylthiazolo[5,4-b]pyridine-2-yl)-3-fluorophenyl)methyl)azetidine-3-carboxylic acid (93.7 mg, 0.209 mmol) was added in one portion, and the resulting suspension was stirred at 50° C. for 20 h. The reaction mixture was then diluted with 0.05M pH 6 phosphate buffer (2.0 mL), acidified with 1.0N HCl (750 μL), diluted with water (15 mL), and partially concentrated in vacuo. The resulting precipitate was collected by vacuum filtration, washed with water (3.0 mL), and dried in vacuo. Reverse-phase HPLC of this solid (C18, CH3CN/H2O+0.1% ammonium formate) afforded 1-((3-fluoro-4-(5-(2-phenyloxetan-2-yl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid as a colorless solid. MS (ESI) m/z: Calculated: 475.1; Observed: 476.1 (M++1).

Provenance & Evidence