(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 650976Notes

Reaction equation

HRID 650976 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-methoxy-phenyl)-ethyl]-amide are dissolved in 420 ml of tetrahydrofuran and, together with 3 g of 5% palladium on active carbon, shaken in a hydrogenation vessel for 5 hours in a hydrogen atmosphere under normal pressure. The catalyst is then filtered off. The filtrate is concentrated. The residue is purified by flash chromatography on silica gel with ethyl acetate/n-hexane 3:1, yielding (S)-2-(ethylsulfonylamino)-3methyl-butyric acid N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide in the form of a colourless oil.

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationThe filtrate is concentrated
  3. customThe residue is purified by flash chromatography on silica gel with ethyl acetate/n-hexane 3:1

Sources & evidence

ORD record
ord-d03a45c0260644a39082a65050c807e2
Source dataset
uspto-grants-2001_08
Patent number
US06277849B1

Reaction notes

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