[C:1]([S:4][C:5]([CH3:45])([CH3:44])[CH:6]([NH:36]C(OC(C)(C)C)=O)[C:7]([O:9][C@H:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[C:23]([O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:22]=1)[CH2:11][C:12]1[C:17]([Cl:18])=[CH:16][N+:15]([O-:19])=[CH:14][C:13]=1[Cl:20])=[O:8])(=[O:3])[CH3:2].Cl.O1CCOCC1>C(Cl)Cl>[C:1]([S:4][C:5]([CH3:45])([CH3:44])[CH:6]([NH2:36])[C:7]([O:9][C@H:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[C:23]([O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:22]=1)[CH2:11][C:12]1[C:13]([Cl:20])=[CH:14][N+:15]([O-:19])=[CH:16][C:17]=1[Cl:18])=[O:8])(=[O:3])[CH3:2]4-((2S)-2-(3-(acetylthio)-2-(tert-butoxycarbonylamino)-3-methylbutanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (118 mg, 0.170 mmol) was dissolved in DCM (1 ml). HCl 4N in dioxane (425 μl, 1.70 mmol) was added and the mixture stirred for 30 minutes at RT. The reaction mixture was diluted with DCM. The organic layer was washed with NaHCO3 sat. sol. (2×) and brine, dried over Na2SO4 and evaporated under vacuum. The crude product was purified by preparative reverse-phase HPLC to give 101 mg of the desired compound (quantitative yield).
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