1-(Phenylmethyl) butanedioate → HCID 59607643, compound

Participants

Reaction Steps

A solution of succinic acid mono-benzyl ester (71.1 mg, 0.342 mmol), EDCl (65.5 mg, 0.342 mmol) and HOAt (46.5 mg, 0.342 mmol) in DMF (1 ml), which is allowed to stir at room temperature for 1 hour, is added to a solution of (R)-3-amino-4-(3′-chlorobiphenyl-4-yl)butanoic acid (66 mg, 0.228 mmol) and DIPEA (0.080 ml, 0.456 mmol) in a mixed solvent DMF (2 ml) and water (2 ml). The reaction mixture is allowed to stir for 3 hours, and then diluted with H2O. The products are extracted twice with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated to give crude. The resulting residue is purified by preparative HPLC using a gradient of 20% MeCN/water (0.1% TFA) to 100% MeCN to give (R)-3-(4-(benzyloxy)-4-oxobutanamido)-4-(3′-chlorobiphenyl-4-yl)butanoic acid (42.4 mg) as a white solid; HPLC retention time=1.22 minutes (condition B); MS (m+1)=480.35; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.44-2.75 (m, 6H) 2.86-2.99 (m, 2H) 4.48-4.56 (m, 1H) 5.11 (s, 2H) 6.29 (br d, J=8.6 Hz, 1H) 6.97-7.07 (m, 10H) 7.25-7.36 (m, 2H) 7.42-7.50 (m, 2H) 7.54 (br t, J=1.6 Hz, 1H).

Provenance & Evidence