Ethyl bromopyruvate → HCID 178470113, compound

HRID 2240330Notes

Reaction equation

HRID 2240330 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH4+].[C:11](=[S:14])([S-:13])[NH2:12]>CCO.CCOC(C)=O>[SH:14][C:11]1[S:13][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:12]=1

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 178470113HCID 178470113, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-bromo-2-oxopropanoate (200 mg, 1.02 mmol) in EtOH (5.0 mL) was added dithiocarbamic acid ammonium salt (96 mg, 1.23 mmol) The reaction mixture was stirred for 16 h, then diluted with EtOAc and washed with H2O and brine. The organic fraction was dried (MgSO4), filtered, and concentrated. Purification by preparative TLC afforded the title compound (45.0 mg, 23%). 1H NMR (DMSO-d6) δ=1.23 (t, 3H), 4.23 (q, 2H), 7.78 (s, 1H); ESIMS: m/z 188 (M+H). mp=120-121° C.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative TLC

Sources & evidence

ORD record
ord-39eb10434d2c463cb845ba6208bc8822
Source dataset
uspto-grants-2010_05
Patent number
US07723366B2

Reaction notes

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