Ethanol → 7-(4-(6-Tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylic acid

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Reaction Steps

Ethyl 7-(4-(6-tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (10 mg, 0.020 mmol) was diluted with THF (200 μL) followed by the addition of NaOH (98 μL, 0.098 mmol) and ethanol (100 μL). After stirring for 3 hours, the reaction was diluted with 0.5N HCl and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a 0.5 mm preparative TLC plate, eluting with 10% methanol/DCM to yield the desired compound (0.8 mg, 0.0017 mmol, 8.5% yield). MS (ESI)=481.2 (M+H).

Provenance & Evidence