(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(dihydroisoxazol-3-yl)propanoyl)oxazolidin-2-one → (S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(dihydroisoxazol-3-yl)propanoyl)oxazolidin-2-one

HRID 2235587Notes

Reaction equation

HRID 2235587 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[CH2:15][C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28]CC2C=CC=CC=2)=[CH:24][CH:23]=1)[CH:17]1[CH:21]=[CH:20][O:19][NH:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[CH2:15][C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH:17]1[CH:21]=[CH:20][O:19][NH:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67330499(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(dihydroisoxazol-3-yl)propanoyl)oxazolidin-2-one

Product 1

HCID 67329489(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(dihydroisoxazol-3-yl)propanoyl)oxazolidin-2-oneYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 9.1 (136 mg) and a catalytic amount of Pd/C in EtOH (2 mL) was stirred at room temperature under 1 atm of H2 for 2.5 hours. The catalyst was removed by filtration, and the filtrate was concentrated to give 9.2 (100 mg). MS ESI (pos.) m/e: 395 (M+H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4797e7a577c841688633653f2ee48207
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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