Methanol → HCID 178473121, compound

HRID 895699Notes

Reaction equation

HRID 895699 reaction equation
CO[C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.Br[CH2:14][C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH3:22]O>CC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[C:15](=[O:21])[CH2:14][S:10][C:8]1[NH:7][C:6]2[CH:11]=[CH:12][C:3]([CH3:22])=[CH:4][C:5]=2[N:9]=1)[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 66144Ethyl bromopyruvateHCID 178488032HCID 178488032, compound

Product 1

HCID 178473121HCID 178473121, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-methoxy-2-benzimidazolethiol (200 mg, 1.11 mmol) and ethyl 3-bromopyruvate (0.20 mL, 1.43 mmol) in methanol (5 mL) and acetone (2 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-Methyl-1H-benzoimidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (300 mg, 92%). 1H-NMR (D3COD, 300 MHz) δ (ppm): 7.19 (br. s, 1H), 6.75 (br. s, 1H), 6.69 (dd, J=2.3 Hz, J=8.8 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 4.29 (br. s, 1H), 3.93 (br. s, 1H), 3.69 (s, 3H), 1.24 (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-9397959250c94ff580eb93ec6c3133ab
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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