Lithium Hydroxide → (2E,4R)-5-(1,1'-Biphenyl)-4-yl-4-(((1,1-dimethylethoxy)carbonyl)amino)-2-methyl-2-pentenoic acid

Participants

Reaction Steps

(E)-(R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester (CAS#149709-59-1) is hydrolysed using lithium hydroxide in ethanol to yield (E)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid as a white solid. δH (400 MHz; DMSO) 1.31 (9H, s, (CH3)3), 1.59 (3H, s, 1-CH3), 2.68 (1H, dd, J 6.8, 13.2, 5-HA), 2.86 (1H, m, 5-HB), 4.44 (1H, m, 4-H), 6.51 (1H, d, J 9.2, 3-H), 7.16 (1H, d, J 8.0, NH), 7.26 (2H, d, J 8.0, Ar-ortho-H(Ph)), 7.31 (1H, t, J 7.6, Ar-(Ph)-para-H), 7.40 (2H, t, J 8.0, Ar-(Ph)-meta-H), 7.54 (2H, d, J 8.0, Ar-meta-H(Ph), 7.60 (2H, d, J 7.6, Ar-(Ph)-ortho-H), 12.26 (1H, s, CO2H); m/z (+ESI) 404 ([MNa]+, 17%), 382 ([MH]+, 2), 326 (10), 264 (100), 167 (13).

Provenance & Evidence