Sodium Hydroxide → (S)-4-((2,4-dichlorophenoxyacetyl)amino)-5-fluoropentanoic acid

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Reaction Steps

0.77 ml of 1N aqueous sodium hydroxide solution was added to a stirred mixture of 0.27 g of 16 in 20 ml of methanol, the resulting mixture was stirred at reflux for one hour and then at room temperature over a week-end. The mixture then was filtered and the solvent evaporated from the filtrate. The residue was placed in water, ethyl acetate was added, then the mixture was acidified with 12N hydrochloric acid. The mixture was stirred for 30 minutes, then the organic phase was separated, dried (Na2SO4) and filtered. The solvent was evaporated from the filtrate to give a pale yellow oil. The oil was filtered through a florosil pad, eluted with ethyl acetate to give an oily solid, which was treated with methanol to give 17, as a white solid.

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