tert-butyl (3S,5S,8S)-8-(benzyloxymethyl)-6-hydroxy-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate → tert-butyl (3S,5S,6S,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate

HRID 660396Notes

Reaction equation

HRID 660396 reaction equation
C([O:8][CH2:9][C@H:10]([CH:43]([CH3:45])[CH3:44])[CH2:11][CH:12]([OH:42])[C@@H:13]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:14][C@H:15]([CH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][N:26]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:22][CH:21]=1)[CH:16]([CH3:18])[CH3:17])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:42][C@@H:12]([CH2:11][C@H:10]([CH2:9][OH:8])[CH:43]([CH3:45])[CH3:44])[C@@H:13]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[CH2:14][C@H:15]([CH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][N:26]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:22][CH:21]=1)[CH:16]([CH3:17])[CH3:18].[OH:42][C@H:12]([CH2:11][C@H:10]([CH2:9][OH:8])[CH:43]([CH3:45])[CH3:44])[C@@H:13]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[CH2:14][C@H:15]([CH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][N:26]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:22][CH:21]=1)[CH:16]([CH3:17])[CH3:18]

Participants

5

Reactant 1

HCID 59630979tert-butyl (3S,5S,8S)-8-(benzyloxymethyl)-6-hydroxy-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate

Product 2

HCID 59630975tert-butyl (3S,5S,6S,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamateYield 30%HCID 59630990tert-butyl (3S,5S,6R,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamateYield 14%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3S,5S,8S)-8-(benzyloxymethyl)-6-hydroxy-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (1.3 g, 2.1 mmol) in methanol 30 mL) was added 20% Pd(OH)2/C (26 mg). The mixture was hydrogenated under a balloon of H2 at rt overnight and filtered. The filtrate was evaporated and purified by preparative HPLC to give tert-butyl (3S,5S,6S,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (0.33 g, 30% yield) as an oil and tert-butyl (3S,5S,6R,8S)-6-hydroxy-8-(hydroxymethyl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (0.15 g, 14%) as an oil. MS: 534 (M++1)

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-90d61042f4e948fe8a94dc9d62f49f2a
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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