Lithium Hydroxide → 2-Hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acid

HRID 1348657Notes

Reaction equation

HRID 1348657 reaction equation
C([O:3][C:4](=[O:17])[C:5]([OH:16])([CH3:15])[C:6]([NH:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[O:7])C.[OH-].[Li+]>O1CCCC1.O>[OH:16][C:5]([CH3:15])([C:6]([NH:8][CH2:9][CH2:10][C:11]([F:12])([F:13])[F:14])=[O:7])[C:4]([OH:17])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86605291HCID 86605291, compound

Product 1

HCID 210914092-Hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acidYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.30 g (7.87 mmol) 2-hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acid ethyl ester in 40 ml of tetrahydrofurane were added 0.33 g (7.87 mmol) of lithium hydroxide in 20 ml of water and the mixture was stirred overnight at room temperature. After concentration in vacuo water (50 ml) was added and the mixture was acidified to pH 1. Extraction with ethylacetate gave 1.46 g (81%) of the title compound as a solid, MS m/e (%): 228.1 (M−H, 100).

Workup

  1. concentrationAfter concentration in vacuo water (50 ml)
  2. additionwas added
  3. extractionExtraction with ethylacetate

Sources & evidence

ORD record
ord-6597474e92504327b3675aec5733b99e
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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