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0 °C

A stirred suspension of (1RS,2SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid (140 mg) in MeOH (5 ml) was cooled to 0° C. and treated with thionyl chloride (10 drops). The mixture turned immediately into a clear solution. Stirring was continued for 3 hrs at 0° C. Then the reaction mixture was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2−>CH2Cl2/MeOH) to give (1RS,2SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid methyl ester (84 mg) as colorless amorphous solid. MS: 353.4 ([M+H]+).

1. concentrationThen the reaction mixture was concentrated
2. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2−>CH2Cl2/MeOH)