Sodium Hydroxide → HCID 67408351, compound

Participants

Reaction Steps

Methyl 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy-n-butyrate (378 mg, 0.782 mmol) was dissolved in THF (20 ml). To the resulting solution was added 0.25N NaOH (20 ml) and the mixture was stirred at 50° C. for 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was acidified with 1N HCl, followed by extraction with a chloroform/methanol (10/1) mixture. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was then purified by thin-layer silica gel column chromatography (TLC), whereby from chloroform/methanol (10/1) eluate fractions, 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)-n-butyric acid (99 mg, 27%) was obtained as a yellow oil. Ethanol (3 ml) and 1N NaOH (211 μl, 0.211 mmol) were added to the resulting 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)-n-butyric acid (99 mg, 0.211 mmol) under stirring to dissolve the latter in the former. The resulting solution was concentrated to dryness. Ether was added to crystallize the residue, whereby sodium 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)-n-butyrate (81 mg) was obtained as a solid.

Provenance & Evidence