Lithium Hydroxide → 3-(1-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoic acid

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Reaction Steps

A solution of methyl 3-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoate (0.031 g, 0.064 mmol) in tetrahydrofuran (0.2 mL) and methanol (0.1 mL) was added 1 M lithium hydroxide solution (0.19 mL, 0.19 mmol) and stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo and the resulting slurry was diluted with water and neutralized (to pH=˜7) with aqueous 1 N HCl solution. The aqueous suspension was extracted with 15% MeOH/CHCl3; the organic extracts were combined, dried (K2CO3), filtered, and concentrated in vacuo. Purification via reverse phase prep. HPLC afforded the title compound as an off-white amorphous solid. MS (ESI) m/z: Calculated: 473.2; Observed: 474.1 (M++1).

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