Tetrahydrofuran → 5'-((1R,2R)-1-Benzyl-2-carboxy-2-hydroxy-ethylcarbamoyl)-2'-fluoro-biphenyl-2-carboxylic Acid

Participants

Reaction Steps

5′-((1R,2R)-1-Benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-2′-fluoro-biphenyl-2-carboxylic acid t-butyl ester (100 mg, 192 μmol, 1.0 eq.) was combined with 1:1 TFA/DCM (1 mL each) and stirred for 1 hour. The solvents were evaporated and THF (3 mL) and 1 M aqueous NaOH (577 μL, 3.0 eq.) were added. The mixture was stirred for 2 hours and EtOAc was added. The aqueous was extracted out and the organic was washed with NaOH (0.2 mL), stirred and the aqueous extracted. The aqueous was acidified to pH ˜5 with concentrated HCl yielding a gummy solid, which was dissolved in AcOH and purified by preparative HPLC to yield the title compound (12.7 mg, 99% purity). MS m/z [M+H]+ calc'd for C24H20FNO6, 438.13. found 438.

Provenance & Evidence