Acetic Acid → HCID 18945288, compound

HRID 399876Notes

Reaction equation

HRID 399876 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8](/[CH:11]=[CH:12]/[C:13]1[N:14]([C:18]2[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=2)[C:21]([N:23]=[C:24]([NH2:26])[NH2:25])=[O:22])[CH:15]=[CH:16][CH:17]=1)([OH:10])=[O:9].C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CCCCCC.O1CCCC1.CO.O.C(OCC)(=O)C>[CH3:1][O:9][C:8](/[CH:11]=[CH:12]/[C:13]1[N:14]([C:18]2[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=2)[C:21]([N:23]=[C:24]([NH2:26])[NH2:25])=[O:22])[CH:15]=[CH:16][CH:17]=1)=[O:10]

Participants

10

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 167693TrimethylsilyldiazomethaneHCID 18945274HCID 18945274, compound

Product 1

HCID 18945288HCID 18945288, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2M (Trimethylsilyl)diazomethane in hexane solution (0.84 ml) was added to a mixture of 2-[3-[2-((E)-2-carboxyethenyl)pyrrol-1-yl]benzoyl]guanidine (0.25 g) in tetrahydrofuran (5 ml) and methanol (5 ml) and the mixture was stirred for 25 minutes at the ambient temperature. To the reaction mixture was added acetic acid (2 ml) and stirred for 5 minutes. The mixture of ethyl acetate and water was added to the above mixture and adjusted to pH 8 with 20% aqueous potassium carbonate solution. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethanol and diisopropyl ether to give 2-[3-[2-((E)-2-methoxycarbonylethenyl)pyrrol-1-yl]benzoyl]guanidine (0.15 g).

Workup

  1. stirringstirred for 5 minutes
  2. additionwas added to the above mixture
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from a mixture of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-3845a6bf7c0b412a9b57458ea2f26d75
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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