3-(S)-(2-(S)-Benzyloxycarbonylamino-4,4-dimethyl-pentanoylamino)-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid tert-butyl ester → 3-(s)-(2-(s)-Benzyloxycarbonylamino-4,4-dimethyl-pentanoylamino)-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid

Participants

Reaction Steps

The title compound of example 158 (46 mg, 83 μmol) was dissolved in a mixture of TFA, dichloromethane and water in a ratio of 45:45:10 (1 mL) and stirred overnight. The solvent was removed and the reaction was lyophilized to afford 58.1 mg (114% of theory) of material that likely had some water or multiple TFA salts included; 1H NMR (MeOD, 400 MHz) δ 0.91 (s, 9H), 1.49 (dd, 1H, J1=9.3, J2=14.4), 1.67 (dd, 1H, J1=3.1, J2=14.5), 2.63 (d, 1H, J=6.5), 2.98 (dd, 1H, J1=J2=8.1), 3.17 (dd, 1H, J1=5.5, J2=13.6), 3.26-3.34 (m, 1H), 3.47 (dd, 1H, J1=8.6, J2=17.3), 3.58 (dd, 1H, J1=8.4, J2=16.6), 4.13 (dd, 1H, J1=3.0, J2=9.3), 4.46-4.55 (m, 1H), 4.98-5.11 (m, 2H), 6.68 (dd, 1H, J1=4.1, J2=8.6), 6.77-6.84 (m, 1H), 6.86-6.91 (m, 1H), 7.24-7:33 (m, 5H); HPLC-MS calcd. for C27H34FN3O5 (M+H+) 500.2, found 500.5.

Provenance & Evidence