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

HRID 660392Notes

Reaction equation

[CH3:1][C:2]([CH3:42])([CH2:38][CH2:39][CH2:40][CH3:41])[C:3]([NH:5][CH2:6][C@H:7]([OH:37])[C@@H:8]([NH:29]C(=O)OC(C)(C)C)[CH2:9][C@H:10]([CH2:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[N:20][N:21]2[CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:17][CH:16]=1)[CH:11]([CH3:13])[CH3:12])=[O:4]>Cl.CO>[NH2:29][C@@H:8]([CH2:9][C@H:10]([CH2:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[N:20][N:21]2[CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:17][CH:16]=1)[CH:11]([CH3:13])[CH3:12])[C@@H:7]([OH:37])[CH2:6][NH:5][C:3](=[O:4])[C:2]([CH3:42])([CH3:1])[CH2:38][CH2:39][CH2:40][CH3:41]

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-183890327aa348bdb47b6f197c9d45ac
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084485B2

Reaction notes

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