(R)-tert-butyl 3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoate → (R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid

Participants

Reaction Steps

To a solution of (R)-tert-butyl 3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoate (40 mg, 0.094 mmol) in DCM (0.5 mL), TFA (0.15 mL) is added at room temperature. The mixture is allowed to stir for 2 hours, and then concentrated under reduced pressure to give (R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid (33.5 mg, 96%). HPLC retention time=1.20 minutes (condition A); MS (m+1)=370.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.21-2.29 (m, 1H) 2.38-2.45 (m, 1H) 2.62-2.66 (m, 1H) 2.75-3.00 (m, 4H) 3.29-3.37 (m, 1H) 3.45-3.53 (m, 4H) 6.12 (br s, 1H) 7.23 (d, J=8 Hz, 2H) 7.32-7.35 (m, 1H) 7.41-7.45 (m, 2H) 7.53 (d, J=8.1 Hz, 2H) 7.56-7.59 (m, 2H).

Provenance & Evidence