(S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-benzyloxy-3-methoxyphenyl)-ethyl]-amide → (S)-2-(Ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide

HRID 636890Notes

Reaction equation

HRID 636890 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:29])[C@@H:19]([NH:23][S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])[CH:20]([CH3:22])[CH3:21])=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:29])[C@@H:19]([NH:23][S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])[CH:20]([CH3:21])[CH3:22])=[CH:11][C:10]=1[O:30][CH3:31]

Participants

5

Reactant 2

HCID 54229772(S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-benzyloxy-3-methoxyphenyl)-ethyl]-amideHCID 178418361HCID 178418361, compound

Product 1

HCID 54471411(S)-2-(Ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

14.5 g of (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-benzyloxy-3-methoxyphenyl)-ethyl]-amide (Ex. P-1. 1) are dissolved in 420 ml of tetrahydrofuran and shaken together with 3 g of palladium-on-carbon (5%) in a duck-shaped hydrogenation vessel for 5 hours in a hydrogen atmosphere at normal pressure. The catalyst is then removed by filtration. The filtrate is concentrated. The residue is purified by flash-chromatography on silica gel using ethyl acetate/n-hexane 3:1, yielding (S)-2-(ethylsulfonylamino)-3-methyl-butyric acid N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-amide in the form of a colourless oil.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationThe filtrate is concentrated
  3. customThe residue is purified by flash-chromatography on silica gel

Sources & evidence

ORD record
ord-11945a1f18cc470bb9e975504862b21f
Source dataset
uspto-grants-2001_02
Patent number
US06194611B1

Reaction notes

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