Ethyl bromoacetate → Glycine, N-[2-(methylsulfonyl)ethyl]-N-(trifluoroacetyl)-, ethyl ester

HRID 2306699Notes

Reaction equation

HRID 2306699 reaction equation
[H-].[Na+].[CH3:3][S:4]([CH2:7][CH2:8][NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])(=[O:6])=[O:5].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C>[CH2:21]([O:20][C:18]([CH2:17][N:9]([CH2:8][CH2:7][S:4]([CH3:3])(=[O:5])=[O:6])[C:10](=[O:15])[C:11]([F:12])([F:14])[F:13])=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 22609710HCID 22609710, compound

Product 1

HCID 22609755Glycine, N-[2-(methylsulfonyl)ethyl]-N-(trifluoroacetyl)-, ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.190 g, 4.75 mmol) was added to a solution of N-(2-methylsulphonylethyl)trifluoroacetamide (0.986 g, 4.50 mmol) in dry DMF (10 ml) and the mixture was stirred under a nitrogen atmosphere for 30 minutes. Ethyl bromoacetate (0.55 ml, 0.828 g, 4.96 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was poured into ice-water, and extracted with ethyl acetate. This solution was washed with water, dried (MgSO4), and concentrated in vacuo to give the title compound as a white solid (1.239 g, 4.03 mmol, 90%); δH CDCl3 4.17 (4H, m), 3.91 (2H, t), 3.46 (2H, t), 2.98 (3H, s), 1.30 (3H, t).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThis solution was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb22b876161b44148f2e4afbbbaba727
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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