1,1'-Carbonyldiimidazole → (1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylate

HRID 1675394Notes

Reaction equation

HRID 1675394 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:12][C@:13]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][C@H:14]1[CH:16]=[CH2:17].[CH:23]1[N:27]=[CH:26][N:25]([C:28](N2C=NC=C2)=[O:29])[CH:24]=1>C1COCC1>[N:25]1([C:28]([NH:12][C@:13]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][C@H:14]2[CH:16]=[CH2:17])=[O:29])[CH:24]=[CH:23][N:27]=[CH:26]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 46737761(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate

Product 1

HCID 57816680(1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate tosylate salt (5 g, 1 eq.) and CDI (2.7 g, 1.1 eq.) were dissolved in THF (50 mL) containing TEA (2.3 mL, 1.1 eq.). The reaction mixture was then refluxed overnight. The solvent was removed under reduced pressure. The residue was dissolved in DCM, and washed twice with water. The organic layer was dried over sodium sulfate and then concentrated. The residue was purified by chromatography on silica gel to yield compound 33 as pale yellow oil in 70% yield.

Workup

  1. temperatureThe reaction mixture was then refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-829828b0f7654fb094befcc549e21ff9
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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