Water → methyl 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoate

Participants

Reaction Steps

EDCI.HCl (0.175 g, 0.915 mmol, 1.1 eq) and HOBT.H2O (0.124 g, 0.915 mmol, 1.1 eq) were added to a stirred solution of 3-(methoxycarbonyl)benzoic acid in 5 ml anhydrous CH2Cl2 at 0° C. under Ar. In a separate flask (2R,3S)-3-amino-1-((5-isopropylpyridin-3-yl)methylamino)-4-phenylbutan-2-ol (0.3118 g, 0.832 mmol, 1.1 eq) in 3 ml anhydrous CH2Cl2 under Ar was treated with DIPEA (1.2 ml, 0.86 g, 6.66 mmol, 8 eq). After both solutions had stirred for 1 h, the active ester was treated with the free-base amine. The reaction was stirred at 0° C. to room temperature overnight. The solvent was removed in vacuo. The residue was partitioned between EtOAc/H2O and the layers were separated. The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo. Purification via flash chromatography yielded 0.274 g (0.58 mmol, 69% yield) of methyl 3-((2S,3R)-3-hydroxy-4-((5-isopropylpyridin-3-yl)methylamino)-1-phenylbutan-2-ylcarbamoyl)benzoate.

Provenance & Evidence