4-(5-Fluoro-2,3-dihydro-indol-1-yl)-3-(S)-[2-(S)-(3-methoxy-benzoylamino)-4,4-dimethyl-pentanoylamino]-butyric acid tert-butyl ester → (3S)-4-(5-fluoro-2,3-dihydro-1H-indol-1-yl)-3-[(2S)-2-[(3-methoxyphenyl)formamido]-4,4-dimethylpentanamido]butanoic acid

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Reaction Steps

The title compound of example 160 (80 mg, 0.14 mmol) 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 partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane 3 times and the combined organics were dried over MgSO4 and the solvent was removed to afford 72 mg (100%) of the title compound as a solid; 1H NMR (MeOD, 400 MHz) δ 0.94 (s, 9H), 1.70 (d, 1H, J=1.1), 2.62 (d, 1H, J=6.5), 2.79-2.93 (m, 2H), 3.06 (dd, 1H, J1=6.0, J2=13.7), 3.19 (dd, 1H, J1=7.7, J2=13.7), 3.45 (dd, 1H, J1=8.6, J2=15.9), 4.42-4.52 (m, 1H), 4.59-4.67 (m, 1H), 6.43 (dd, 1H, J1=4.2, J2=8.5), 6.62-6.68 (m, 1H), 6.72-6.78 (m, 1H), 7.05-7.08 (m, 1H), 7.29-7.38 (m, 3H), 7.96 (d, 1H, J=8.6), 8.37 (d, 1H, J=8.2); HPLC-MS calcd. for C27H34FN3O5 (M+H+) 500.2, found 500.5.

Provenance & Evidence