Imidazole → HCID 12849636, compound

HRID 1980637Notes

Reaction equation

HRID 1980637 reaction equation
C([S:4][C:5]1[S:11][CH:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[C:6]=1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])(=O)C.N1C=CN=C1>O1CCOCC1.O>[O:12]=[C:8]1[N:7]2[CH:10]([S:11][C:5](=[S:4])[CH:6]2[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)=[O:14])[CH2:9]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 12849635HCID 12849635, compound

Product 1

HCID 12849636HCID 12849636, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 100 mg of 4-nitrobenzyl 3-acetylthio-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in a mixture of 2 ml of dioxane and 0.2 ml of water was added 19.6 mg of imidazole. After 10 minutes the reaction mixture was diluted with 5 ml of 1M aqueous acid solution and extracted with dichloromethane (2×5 ml). The organic extracts were combined and backwashed with water (2×5 ml), then brine (5 ml), and finally dried and evaporated. The residue was chromatographed on slica gel, with elution by means of ethyl acetate/hexane mixtures. Fractions containing the purified product were combined and evaporated to leave an orange oil (43 mg, 48%).

Workup

  1. extractionextracted with dichloromethane (2×5 ml)
  2. dry with materialbrine (5 ml), and finally dried
  3. customevaporated
  4. customThe residue was chromatographed on slica gel, with elution by means of ethyl acetate/hexane mixtures
  5. additionFractions containing the purified product
  6. customevaporated

Sources & evidence

ORD record
ord-82dd1f4cc8a64fe4bc1b2a3df78eafdf
Source dataset
uspto-grants-1985_04
Patent number
US04510086

Reaction notes

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