Sodium Hydroxide → HCID 3477613, compound

Participants

Reaction Steps

A mixture of (RS)-5-(4-Benzyloxy-phenyl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester 78 (0.86 g, 1.7 mmol) and NaOH solution (4 M, 0.85 mL, 3.4 mmol) in MeOH-THF (1:1, 6 mL) was stirred at room temperature overnight. The solvent was removed, and the residue diluted with water. The solution was washed with Et2O, acidified with 5% aqueous HCl, and extracted with EtOAc. The organic phase was then washed with brine, dried (Na2SO4) and the solvent removed under reduced pressure to afford 85 (0.81 g, 98%), m.p. 127.7-129.5° C. 1H NMR (DMSO-d6) δ 1.13-1.23 (m, 6H), 1.35-1.44 (m, 2H), 1.47-1.54 (m, 2H), 1.95-2.00 (m, 2H), 2.14-2.22 (m, 2H), 3.86 (br s, 1H), 5.02 (s, 2H), 6.89 (d, J=8.6 Hz, 2H), 7.08 (d, J=8.5 Hz, 2H), 7.15-7.44 (m, 10H), 7.50 (br d, J=8.6 Hz, 1H), 12.01 (br s, 1H). 13C NM (DMSO-d6) δ 174.3, 171.7, 156.7, 142.3, 137.2, 131.1, 130.1, 128.4, 128.2, 127.8, 127.7, 125.6, 114.3, 49.3, 35.5, 35.2, 31.0, 30.5, 29.3, 28.5, 28.4, 25.3. ESMS 488 (M+H)+.

Provenance & Evidence