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

HRID 1348654Notes

Reaction equation

HRID 1348654 reaction equation
C([O:3][C:4](=[O:16])[C:5]([OH:15])([CH3:14])[C:6]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])C.[OH-].[Li+]>O1CCCC1.O>[OH:15][C:5]([CH3:14])([C:6]([NH:8][CH2:9][C:10]([F:11])([F:12])[F:13])=[O:7])[C:4]([OH:16])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86605290HCID 86605290, compound

Product 1

HCID 210914072-Hydroxy-2-methyl-N-(2,2,2-trifluoro-ethyl)-malonamic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.60 g (15.0 mmol) (S or R)-2-hydroxy-2-methyl-N-(2,2,2-trifluoro-ethyl)-malonamic acid ethyl ester, entity A, in 50 ml of tetrahydrofurane were added 0.65 g (16 mmol) of lithium hydroxide in 25 ml of water and the mixture was stirred for 18 hours at room temperature. After removal of the organic solvent by distillation the mixture was acidified to pH 1. Extraction with ethylacetate gave 2.70 g (85%) of the title compound as an oil, MS m/e (%): 214.3 (M−H, 100).

Workup

  1. customAfter removal of the organic solvent
  2. distillationby distillation the mixture
  3. extractionExtraction with ethylacetate

Sources & evidence

ORD record
ord-eca943983e924e3e8e723f3f96e2d01d
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

Loading…