Methanol → HCID 178473123, compound

HRID 895698Notes

Reaction equation

HRID 895698 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9](C)[CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:21][OH:22]>CC(C)=O>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[O:20])[CH2:13][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:22][CH3:21])=[CH:10][C:4]=2[N:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 66144Ethyl bromopyruvateHCID 178423448HCID 178423448, compound

Product 1

HCID 178473123HCID 178473123, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-mercapto-5-methylbenzimidazole (200 mg, 1.22 mmol) and ethyl 3-bromopyruvate (0.20 mL, 1.43 mmol) in methanol (2 mL) and acetone (3 mL) was shaken at room temperature 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-(5-methoxy-1H-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (300 mg, 88%). 1H-NMR (D3COD, 300 MHz) δ (ppm): 7.19 (br. s, 1H), 7.10 and 7.04 (br. 2 s, 1H), 6.94 (d, J=8.2 Hz, 1H), 4.34 (q, J=7.1 Hz, 2H), 4.31 (br. s, 1H), 3.91 (br. s, 1H), 2.37 (br. s, 3H), 1.26 (t, J=7.1 Hz, 3H).

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-9b0170aa5fcf44b0b6ffa7a970ce173e
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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