Methyl iodide → 1-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide

HRID 420031Notes

Reaction equation

HRID 420031 reaction equation
[CH3:1][I:2].[N:3]1([C:8]([NH:10][C@:11]2([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][C@H:12]2[CH:14]=[CH2:15])=[O:9])[CH:7]=[CH:6][N:5]=[CH:4]1>C(#N)C>[I-:2].[CH2:19]([O:18][C:16]([C@@:11]1([NH:10][C:8]([N:3]2[CH:7]=[CH:6][N+:5]([CH3:1])=[CH:4]2)=[O:9])[CH2:13][C@H:12]1[CH:14]=[CH2:15])=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57816680(1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylate

Product 1

HCID 866332061-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, methyl iodide (1.9 mL, 4 eq.) was added to a solution of compound 33 (2 g, 1 eq.) in ACN (16 mL). The reaction mixture was stirred at room temperature for 2 hrs. The solvent was removed under reduced pressure to yield compound 34 as yellow oil, which was used directly in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a90f5bdb29fa4ead9beb589f411e8a5d
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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