1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate → 1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-(3-(methyloxy)propyl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 2078311Notes

Reaction equation

HRID 2078311 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[CH2:14][O:15][CH3:16])=[CH:9][CH:10]=2)[C:5]([CH3:18])([CH3:17])[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21]>CCO.[Pd]>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:9][CH:10]=2)[C:5]([CH3:18])([CH3:17])[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21]

Participants

4

Reactant 1

HCID 670998541,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 670998621,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-(3-(methyloxy)propyl)-2-oxo-naphthalen-3-yl)carbonyl)glycinateYield 115.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 1,1-dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate (245 mg, 590 μmol, Example 98A) in EtOH (5897 μL), was added palladium (10 wt. % on activated carbon (62.8 mg, 590 μmol)) at ambient temperature. The mixture was placed under hydrogen gas using a balloon, and the reaction mixture was stirred for 1.5 hours before it was filtered through a pad of Celite, washed with DCM, and concentrated to give the title compound (284 mg) as a light yellow oil. MS m/e=440 (M+Na)+.

Workup

  1. filtrationwas filtered through a pad of Celite
  2. washwashed with DCM
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b70436a3be6841658c76d83913e7631e
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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