Di-tert-butyl (4R)-4-{[5-(benzyloxy)pyridin-2-yl]methyl}-N-(tert-butoxycarbonyl)-L-glutamate → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate

HRID 591283Notes

Reaction equation

HRID 591283 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:17][C@@H:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:23]([O:22][C:20]([NH:19][C@H:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:17][C@H:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1)[C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 70957109Di-tert-butyl (4R)-4-{[5-(benzyloxy)pyridin-2-yl]methyl}-N-(tert-butoxycarbonyl)-L-glutamate

Product 1

HCID 70957058Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 610 mg (1.10 mmol) of di-tert-butyl (4R)-4-{[5-(benzyloxy)pyridin-2-yl]methyl}-N-(tert-butoxycarbonyl)-L-glutamate in methanol (35 mL) was added a 10% palladium on charcoal catalyst (29 mg), and the resulting suspension was stirred overnight under an atmosphere of hydrogen at room temperature. The catalyst was removed by filtration, and the filtrate was evaporated to give 500 mg of the pure target compound as colorless foam (98% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5f595728438448d1b0546d0bbcb73b02
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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