m-Chloroperbenzoic acid → HCID 59174893, compound

Participants

Reaction Steps

A slurry of 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-phenyl)methyl)azetidine-3-carboxylic acid (0.084 g, 0.18 mmol) and mCPBA (0.063 g, 0.37 mmol) in 5 mL 10% MeOH/DCM was stirred rapidly at ambient temperature. After about 10 min, the reaction mixture became clear. After 10 additional minutes precipitates formed. After 10 additional minutes, the reaction mixture was filtered, rinsing with DCM. The solid was collected and dried in vacuo to give 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid N-oxide as a mixture of isomers. The isomers were separated by RPHPLC (A=0.2% formic acid in water; B=0.04% formic acid in acetonitirle; 30×100, Gemini Axia, Sum) to give (1r,3s)-3-carboxy-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine 1-oxide and (1s,3r)-3-carboxy-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine 1-oxide. MS (ESI) m/z: Calculated: 475.1; Observed: 476.1 (M++1).

Provenance & Evidence