Ethyl bromopyruvate → HCID 9835036, compound

HRID 2183563Notes

Reaction equation

HRID 2183563 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CO.CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH2:12][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1)[CH3:18]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 178527775HCID 178527775, compound

Product 1

HCID 9835036HCID 9835036, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A solution of 2-mercaptobenzimidazole (200 mg, 1.33 mmol) and ethyl 3-bromopyruvate (0.20 mL, 1.43 mmol) in methanol (2.5 mL) and acetone (2 mL) was shaken at 20° C. for 4 hours. The solvents were removed under the reduced pressure on a rotary evaporator. The residue was triturated with ethyl acetate. Solvent was decanted and the residue was dissolved in methylene chloride. The solution was washed with diluted aqueous sodium bicarbonate solution and water, and then dried over magnesium sulfate. Removal of the solvent gave the expected product, 3-(1H-Benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (326 mg, 93%). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 7.31 (br. s, 1H), 7.24 (br s, 1H), 7.15-7.05 (m, 2H), 4.32 (q, J=7.1 Hz, 2H), 4.29 (br. s, 1H), 3.90 (br. s, 1H), 1.24 (t, J=7.1 Hz, 3H). MS (ESI): m/z 265 (M+1, 100).

Workup

  1. customThe solvents were removed under the reduced pressure on a rotary evaporator
  2. customThe residue was triturated with ethyl acetate
  3. customSolvent was decanted
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThe solution was washed with diluted aqueous sodium bicarbonate solution and water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-c9457b3decfd4870bb37af0f4b476645
Source dataset
uspto-grants-2005_05
Patent number
US06900218B2

Reaction notes

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