Methanol → 5-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

HRID 1349475Notes

Reaction equation

HRID 1349475 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:36])[C:11]([C:32]([O:34]C)=[O:33])=[CH:12][N:13]([CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:36])[C:11]([C:32]([OH:34])=[O:33])=[CH:12][N:13]([CH2:26][CH:27]([O:28][CH3:29])[O:30][CH3:31])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 23077726Methyl 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 230776405-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acidYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (2.0 g) in tetrahydrofuran (20 ml)-methanol (10 ml) was added 4N aqueous lithium hydroxide solution (1.5 ml) and the mixture was stirred at 70° C. for 1 hr. The precipitated solid was removed by thin layer of celite and washed with methanol. The solvent was evaporated and 1N aqueous hydrochloric acid (6.5 ml) and water (50 ml) were added. The mixture was extracted twice with ethyl acetate (75 ml each). The ethyl acetate layer was dried, concentrated and crystallized from ethyl acetate-diisopropyl ether to give 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (1.2 g).

Workup

  1. customThe precipitated solid was removed by thin layer of celite
  2. washwashed with methanol
  3. customThe solvent was evaporated
  4. addition1N aqueous hydrochloric acid (6.5 ml) and water (50 ml) were added
  5. extractionThe mixture was extracted twice with ethyl acetate (75 ml each)
  6. dry with materialThe ethyl acetate layer was dried
  7. concentrationconcentrated
  8. customcrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-befb68c3e0134c0b9cf6bfc7617158eb
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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