Sodium Hydroxide → (2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid

Participants

Reaction Steps

To a solution of (2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate (0.100 g, 0.17 mmol) in 2 mL THF was added sodium hydroxide (0.70 mL, 0.70 mmol). The yellow cloudy reaction mixture was diluted with 0.7 mL water, and stirred rapidly at ambient temperature. After 6 h, the reaction mixture was quenched with ice and 5 N HCl until slightly acidic. The aq. Layer was extracted with DCM and the combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give (2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid as a white solid. MS (ESI) m/z: Calculated: 559.2; Observed: 559.7 (M++1).

Provenance & Evidence