tert-butyl (2S,3S,5S)-1-(2,2-dimethylhexanamido)-2-hydroxy-5-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-6-methylheptan-3-ylcarbamate → N-((2S,3S,5S)-3-amino-2-hydroxy-5-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-6-methylheptyl)-2,2-dimethylhexanamide

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (2S,3S,5S)-1-(2,2-dimethylhexanamido)-2-hydroxy-5-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-6-methylheptan-3-ylcarbamate (335 mg, 75%) (83 mg, 0.15 mmol) was dissolved in a solution of 2N HCl in methanol (6 mL) and the reaction mixture was stirred at 40° C. for 2 h. The solvent was removed in vacuo to produce N-((2S,3S,5S)-3-amino-2-hydroxy-5-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-6-methylheptyl)-2,2-dimethylhexanamide (58 mg, 80%). 1H NMR (400 MHz, CDCl3): 0.86 (m, 3H), 0.92 (m, 3H), 0.99 (m, 3H), 1.13 (s, 6H), 1.16 (m, 2H), 1.27 (m, 3H), 1.49 (m, 2H), 1.70 (m, 3H), 1.88 (m, 1H), 2.11 (m, 2H), 2.62 (m, 1H), 2.85 (m, 1H), 2.97 (m, 1H), 3.10 (m, 1H), 3.28 (s, 3H), 3.36 (m, 1H), 3.64 (m, 1H), 4.49 (m, 2H), 7.06 (d, 1H), 7.39 (s, 1H), 7.67 (d, 1H), 7.97 (s, 1H); MS: 488 (M+1).

Provenance & Evidence