Lithium Hydroxide → N-(2-fluoroethyl)-N-methyloxamic acid

HRID 1093035Notes

Reaction equation

HRID 1093035 reaction equation
[F:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[C:6]([O:8]CC)=[O:7].[Li+].[OH-]>CO.O>[F:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86634927Ethyl 2-((2-fluoroethyl)(methyl)amino)-2-oxoacetate

Product 1

HCID 55301814N-(2-fluoroethyl)-N-methyloxamic acidYield 56%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of ethyl 2-((2-fluoroethyl)(methyl)amino)-2-oxoacetate (1.2 g, 7.36 mmol) in methanol/water (30 mL, 1:1) was added LiOH (0.352 g, 14.71 mmol). The solution was stirred for 2 h. The methanol was removed by concentration and concentrated HCl (2 mL) was added. The solvent was removed and the residue dissolved in CH2Cl2 and filtered. The filtrate was concentrated to give the title compound as an off-white crystalline powder (0.615 g, 56% yield). 1H NMR (400 MHz, CDCl3) δ: 4.47-4.89 (2 H, m) 3.67-4.39 (2 H, m) 3.07-3.60 (3 H, m).

Workup

  1. customThe methanol was removed by concentration and concentrated HCl (2 mL)
  2. additionwas added
  3. customThe solvent was removed
  4. dissolutionthe residue dissolved in CH2Cl2
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e959f6e3c945458ea2af07eda1ca0a8e
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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