Hydrochloric Acid → HCID 57905251, compound

HRID 1093032Notes

Reaction equation

HRID 1093032 reaction equation
[CH3:1][N:2]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:3](=[O:8])[C:4]([O:6]C)=[O:5].[Li+].[OH-].Cl>CO.O>[CH3:1][N:2]([CH2:9][C:10]([F:11])([F:12])[F:13])[C:3](=[O:8])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86634926HCID 86634926, compound

Product 1

HCID 57905251HCID 57905251, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(methyl(2,2,2-trifluoroethyl)amino)-2-oxoacetate (1.2 g, 6.03 mmol) in methanol (15 mL) and water (15.00 mL) was added LiOH (0.506 g, 12.05 mmol) and the mixture stirred for 2 h. The solution was then acidified with conc. HCl and concentrated. The solid was washed with CH2Cl2 (2×100 mL), filtered and the filtrate concentrated to afford the title compound (600 mg, 53.8% yield) (mixture of rotational isomers at room temperature) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ: 4.32 (1 H, q, J=9.36 Hz), 4.23 (1 H, q, J=9.46 Hz), 3.07 (2 H, s), 2.97 (1 H, s).

Workup

  1. concentrationconcentrated
  2. washThe solid was washed with CH2Cl2 (2×100 mL)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-c6663d1193e348809e2ead6a0dd7df97
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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