Methyl iodide → HCID 53832157, compound

HRID 1897625Notes

Reaction equation

HRID 1897625 reaction equation
I[CH3:2].[CH3:3][N:4]1[CH:14]=[N:13][C:6]([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:5]1>C(#N)C>[CH3:3][N:4]1[CH2:14][N:13]([CH3:2])[C:6]([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:5]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 921051-Methyl-L-histidine

Product 1

HCID 53832157HCID 53832157, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methylated histamine and histidine are also expected to have low toxicity because histamine and histidine occur naturally in the body. The reaction of L-histidine methyl ester dihydrochloride 28 with carbonyldiimidazole in DMF results in 29. The combination of three equivalents of iodomethane with 29 in refluxing acetonitrile gives 30. The iodide salt of 30 is reacted with methanol in the presence of N,N-diisopropylethylamine at reflux for 3 days to obtain 1-methyl-L-histidine 31. The combination of three equivalents of iodomethane with compound 31 in refluxing acetonitrile gives 1,3-dimethyl-L-histidine 32. The combination of 32 with Ag2O in DMSO forms the silver carbene complex 33. Compound 33b has been shown to have significant antimicrobial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa by the Kirby-Bauer technique.

Sources & evidence

ORD record
ord-33b2b86276894f6d9ddff54b8c6ce195
Source dataset
uspto-grants-2013_08
Patent number
US08519146B2

Reaction notes

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