Lithium Hydroxide → 3-[Benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)propanoic acid

Participants

Reaction Steps

Benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acid (62 mg; 0.13 mmol) was dissolved in THF (1 mL) and water (1 mL). LiOH (12 mg; 0.5 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated, water (1 mL) was added and the aqueous solution was extracted with CHCl3 (1×1 mL). 0.5 M aqueous HCl (1 mL) was added to the aqueous solution, and the resulting acidic aqueous solution was extracted with CHCl3 (3×2 mL). The combined organic phases were dried and concentrated to afford 46 mg (81%) of 3-[benzyl(hydroxy)phosphoryl]-2-({6-[(tert-butoxycarbonyl)amino]-pyridin-3-yl}methyl)propanoic acid.

Provenance & Evidence