Sodium Hydroxide → 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoic acid

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Reaction Steps

methyl 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoate (0.060 g, 0.126 mmol, 1 eq) was dissolved in 2 ml of 1:1 MeOH/THF. 1N NaOH (0.158 ml, 0.158 mmol, 1.25 eq) was added and the reaction was stirred over the weekend. The solvent was removed in vacuo. 1N HCl was added to pH {tilde over ( )} 3-4. The mixture was diluted with 10% MeOH in CHCl3 and dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo yielding 0.055 g (0.119 mmol, 95% yield) of 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoic acid.

Provenance & Evidence