Potassium Carbonate → HCID 86714635, compound

HRID 1409350Notes

Reaction equation

HRID 1409350 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][C@H:19]1[CH2:21][O:20]1>CN(C=O)C>[OH:20][C@@H:19]([CH3:21])[CH2:18][N:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146262(2S)-2-Methyloxirane2×HCID 178469895HCID 178469895, compound

Product 1

HCID 86714635HCID 86714635, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 2-methyl-1H-imidazole-4-carboxylate (1.622 mmol, 250 mg) and potassium carbonate (16.22 mmol, 2241 mg) were dissolved in dry DMF (5 ml) under nitrogen atmosphere. (S)-2-methyloxirane (24.32 mmol, 1.723 ml) was added and the resulting mixture was heated to 60° C. and stirred for 5.5 h. More (S)-2-methyloxirane (1 ml) was added and the stirring continued at 60° C. for one additional hour. The solvent was evaporated. The crude product was purified by flash chromatography. 139 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.06 (d, 3H), 1.24 (t, 3H), 2.30 (s, 3H), 3.71-3.89 (m, 4H), 4.18 (q, 2H), 7.73 (s, 1H).

Workup

  1. customcontinued at 60° C. for one additional hour
  2. customThe solvent was evaporated
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-8babebbb335e4397b3cc7c773c3df4e4
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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