3-Benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide → 1-(2,2-Dimethoxyethyl)-3-hydroxy-5-isopropyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide

HRID 1349481Notes

Reaction equation

HRID 1349481 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:27][CH:28]([O:31][CH3:32])[O:29][CH3:30])[CH:11]=[C:12]([C:24]([CH3:26])=[CH2:25])[C:13](=[O:23])[C:14]=1[O:15]CC1C=CC=CC=1)=[O:8].[H][H]>CO.[C].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:27][CH:28]([O:31][CH3:32])[O:29][CH3:30])[CH:11]=[C:12]([CH:24]([CH3:25])[CH3:26])[C:13](=[O:23])[C:14]=1[OH:15])=[O:8]

Participants

5

Reactant 2

HCID 588591333-Benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 588591361-(2,2-Dimethoxyethyl)-3-hydroxy-5-isopropyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamideYield 87.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (60 mg) in methanol (1 ml) was added 5% palladium-carbon (20 mg) and the mixture was stirred under an atmospheric pressure of hydrogen for 16 hr. A solid was filtered off and the filtrate was concentrated to give 1-(2,2-dimethoxyethyl)-3-hydroxy-5-isopropyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (43 mg).

Workup

  1. filtrationA solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-27bfdafcd4974373a99eddbcdeee84d7
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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