Sodium Hydroxide → (3-Carbamoyl-1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-1H-indol-6-yloxy)-acetic acid

Participants

Reaction Steps

To a solution of (3-carbamoyl-1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-1H-indol-6-yloxy)-acetic acid methyl ester Example 592 (18 mg, 0.032 mmol) in a mixture of THF (2 mL) and water (0.2 mL) was added 1N NaOH (0.064 mL), followed by stirring at RT for 4 h. The reaction mixture was partitioned between CH2Cl2 and water. The aqueous phase was adjusted to pH=2 by addition of 1N HCl, followed by extraction with CH2Cl2 (3×). The combined organics were dried (phase separator) and concentrated under reduced pressure to afford the title compound as a white solid. MS: 549 [M+H]+; tR (HPLC conditions c): 3.74 min.

Provenance & Evidence