Sodium hydride → 2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4-dimethylpentanoic acid

HRID 56808Notes

Reaction equation

HRID 56808 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:35]#[N:36])=[C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][N:13]([CH:18]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:19]([O:21]CC3C=CC=CC=3)=[O:20])[C:12](=[O:34])[CH:11]=2)[CH:9]=1>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:35]#[N:36])=[C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][N:13]([CH:18]([CH2:29][C:30]([CH3:32])([CH3:33])[CH3:31])[C:19]([OH:21])=[O:20])[C:12](=[O:34])[CH:11]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 118877930Benzyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4-dimethylpentanoate

Product 1

HCID 1188778972-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4-dimethylpentanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.5 mg (438 μmol, 60% in mineral oil) of sodium hydride were added to a solution of 140 mg (292 μmol) of benzyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4-dimethylpentanoate (racemate) in 5 ml of THF (not dry), and the mixture was stirred for another 15 min. The reaction was terminated by addition of 5 ml of saturated aqueous ammonium chloride solution, 10 ml of dichloromethane and 0.5 ml of hydrochloric acid (1N). The phases were separated and the aqueous phase was extracted three times with 5 ml of dichloromethane. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The residue corresponded to the title compound and was used for the next step without further purification. Yield: 110 mg (83% of theory, purity 86%)

Workup

  1. customdry), and the mixture
  2. customThe reaction was terminated by addition of 5 ml of saturated aqueous ammonium chloride solution, 10 ml of dichloromethane and 0.5 ml of hydrochloric acid (1N)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted three times with 5 ml of dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-f3b2f048ccc5482eac7fcf72e66720fa
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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