Methyl iodide → 3-{(S)-2-Methoxycarbonylpyrrolidine-1-carbonyl}-3-methyl-1H-imidazol-3-ium iodide

HRID 43746Notes

Reaction equation

HRID 43746 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[O:10].[CH3:17][I:18]>C(#N)C>[I-:18].[CH3:1][O:2][C:3]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([N+:11]1([CH3:17])[CH:15]=[CH:14][NH:13][CH2:12]1)=[O:10])=[O:16]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 675488891-(1H-Imidazol-1-ylcarbonyl)-L-proline methyl ester

Product 1

HCID 675491403-{(S)-2-Methoxycarbonylpyrrolidine-1-carbonyl}-3-methyl-1H-imidazol-3-ium iodideYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(1H-Imidazol-1-ylcarbonyl)-L-proline methyl ester obtained in Example (151a) (0.200 g, 0.896 mmol) was dissolved in acetonitrile (2 ml). Methyl iodide (0.508 g, 3.58 mmol) was added, and the mixture was stirred at room temperature for 24 hours. The reaction solution was concentrated under reduced pressure to obtain 0.327 g of the title compound as a pale yellow foamy substance (100%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1097c4aa5e6c4d1f977dc8c0a1b19c61
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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