Water → HCID 69650218, compound

HRID 1789926Notes

Reaction equation

HRID 1789926 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH:11]([C:15]1[CH:16]=[N:17][C:18]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:20]=1)[CH2:12][CH2:13][CH3:14])[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+].O>ClCCl.C(O)C.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH:11]([C:15]1[CH:16]=[N:17][C:18]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:20]=1)[CH2:12][CH2:13][CH3:14])[C:6]([OH:8])=[O:7])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 69650395HCID 69650395, compound

Product 1

HCID 69650218HCID 69650218, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

This crude 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-malonic acid diethyl ester was dissolved in a mixture of dichloromethane (2.5 mL) and ethanol (5 mL) at 0° C. and a solution of potassium hydroxide (87%, 111 mg, 5.4 mmol) in ethanol (4 mL) was added. The mixture was allowed to warm up slowly to room temperature and stirring was continued for 24 h. Then dichloromethane (20 mL), water (20 mL) and brine (3 mL) was added. The mixture was stirred vigorously for 2 min. Then the layers were separated, the aqueous was washed with dichloromethane. The combined aqueous layers were acidified (pH 5) with citric acid, and extracted three times with dichloromethane. The combined organic layers were washed with brine and dried. Concentration under reduced pressure gave crude 2-[1-{6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-malonic acid monoethyl ester (258 mg, 41%).

Workup

  1. stirringThe mixture was stirred vigorously for 2 min
  2. customThen the layers were separated
  3. washthe aqueous was washed with dichloromethane
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-f22ffc0d44394ac888688756a345b4ba
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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