Potassium Carbonate → HCID 86714631, compound

HRID 1409342Notes

Reaction equation

HRID 1409342 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+].[CH2:18]1[O:21][C@@H:19]1[CH3:20]>CN(C=O)C>[OH:21][C@H:19]([CH3:20])[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 146261(R)-1,2-Epoxypropane2×HCID 178469895HCID 178469895, compound

Product 1

HCID 86714631HCID 86714631, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 2-methyl-1H-imidazole-4-carboxylate (3.24 mmol, 500 mg) and potassium carbonate (32.4 mmol, 4482 mg) were dissolved in DMF (10 ml). (R)-(+)-propylene oxide (48.6 mmol, 3.41 ml) was added and the resulting mixture was stirred at 60° C. for 5.5 h. More (R)-(+)-propylene oxide (1.5 ml) was added and the heating continued for another hour. The mixture was evaporated and the residue was purified by flash chromatography. 525 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.06 (d, 3H), 1.25 (t, 3H), 2.30 (s, 3H), 3.68-4.00 (m, 3H), 4.18 (q, 2H), 4.95 (d, 1H), 7.73 (s, 1H).

Workup

  1. waitthe heating continued for another hour
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-638f423ae590427face3b108897bb0a6
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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