(S)-2-(tert-butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-(4-benzyloxy-3-methoxy-phenyl)-ethyl]-amide → (S)-2-(tert-butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide

HRID 1018654Notes

Reaction equation

HRID 1018654 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:31])[C@@H:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:20]([CH3:22])[CH3:21])=[CH:11][C:10]=1[O:32][CH3:33])C1C=CC=CC=1>O1CCCC1.[H][H].[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:31])[C@@H:19]([NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH:20]([CH3:22])[CH3:21])=[CH:11][C:10]=1[O:32][CH3:33]

Participants

5

Reactant 1

HCID 53964797(S)-2-(tert-butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-(4-benzyloxy-3-methoxy-phenyl)-ethyl]-amide

Product 1

HCID 57264564(S)-2-(tert-butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

50.4 g of (S)-2-(tert-butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-(4-benzyloxy-3-methoxy-phenyl)-ethyl]-amide are dissolved in 1000 ml of tetrahydrofuran and hydrogenated with hydrogen for 2 hours over 10 g of 10% palladium on activated carbon under normal pressure and at room temperature. Filtration with suction is carried out over Celite. The filtrate is concentrated by evaporation, yielding (S)-2-(tert-butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide in the form of an oil.

Workup

  1. filtrationFiltration with suction
  2. concentrationThe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-69d35870272846219b623e8ad15217f1
Source dataset
uspto-grants-2002_11
Patent number
US06482859B1

Reaction notes

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