Lithium Hydroxide → N-(3,5-difluoro-benzyl)-2-methyl-malonamic acid

HRID 2223242Notes

Reaction equation

HRID 2223242 reaction equation
C([O:3][C:4](=[O:19])[CH:5]([CH3:18])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)=[O:7])C.[OH-].[Li+]>C(O)C.O>[F:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([F:17])[CH:13]=1)[CH2:9][NH:8][C:6](=[O:7])[CH:5]([CH3:18])[C:4]([OH:19])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69280082N-(3,5-Difluoro-benzyl)-2-methyl-malonamic acid ethyl ester

Product 1

HCID 21091473N-(3,5-difluoro-benzyl)-2-methyl-malonamic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.0 g (14.75 mmol) N-(3,5-difluoro-benzyl)-2-methyl-malonamic acid ethyl ester in 300 ml of ethanol, 15 ml of water and 1.41 g (59 mmol) of lithium hydroxide were added and the mixture was refluxed for 5 hours. After concentration in vacuo water (50 ml) was added and the mixture was extracted with dichloromethane (three times 30 ml). The aqueous phase was acidified with 8 N hydrochloric acid and extracted with dichloromethane (four times 30 ml).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. concentrationAfter concentration in vacuo water (50 ml)
  3. additionwas added
  4. extractionthe mixture was extracted with dichloromethane (three times 30 ml)
  5. extractionextracted with dichloromethane (four times 30 ml)

Sources & evidence

ORD record
ord-45e91b0a0d784d0c84933259972d1081
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

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