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

HRID 1675395Notes

Reaction equation

HRID 1675395 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-d7249a37462846cf819c763a58c5eacd
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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