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

HRID 1425220Notes

Reaction equation

HRID 1425220 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-67cab8c4fd30493eb2f76cf0a3070fe2
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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