Potassium Carbonate → benzyl N-[1-[(Z)-N'-hydroxycarbamimidoyl]cyclopropyl]carbamate

HRID 1040497Notes

Reaction equation

HRID 1040497 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C:11]1([C:14]#[N:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19].C([O-])([O-])=O.[K+].[K+]>CCO>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C:11]1([C:14](=[NH:15])[NH:18][OH:19])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 57916539HCID 57916539, compound

Product 1

HCID 178513407benzyl N-[1-[(Z)-N'-hydroxycarbamimidoyl]cyclopropyl]carbamateYield 15.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1-cyano-cyclopropyl)-carbamic acid benzyl ester (3.7 g, 17.11 mmol) in EtOH (40 mL) was added hydroxylamine hydrochloride (3.6 g, 51 mmol) and K2CO3 (9.5 g, 68 mmol). The reaction mixture was heated at reflux for 24 h. The resulting white suspension was cooled to RT and concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered, concentrated and purified by reverse phase HPLC to give [1-(N-hydroxycarbamimidoyl)-cyclopropyl]-carbamic acid benzyl ester (0.68 g, 2.7 mmol) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc (3×100 mL)
  6. washThe combined extracts were washed with water, brine
  7. dry with materialdried with MgSO4
  8. filtrationThe mixture was filtered
  9. concentrationconcentrated
  10. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-fc3d154df39d4afc9d2a47e64a3d08d9
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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