Sodium Hydroxide → HCID 22100508, compound

HRID 1457971Notes

Reaction equation

HRID 1457971 reaction equation
C([O:3][C:4]([C:6]12[CH2:12][CH2:11][CH:10]1[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7]2)=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:16]([O:15][C:13]([N:8]1[CH2:9][CH:10]2[C:6]([C:4]([OH:5])=[O:3])([CH2:12][CH2:11]2)[CH2:7]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 221005171-Ethoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane

Product 1

HCID 22100508HCID 22100508, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 825 mg (2.60 mmol) of 1-ethoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane in ethanol (10 ml) cooled in an ice bath was added 5 ml of 1N sodium hydroxide aqueous solution, followed by 2 hours of stirring at room temperature. After neutralization with 1N hydrochloric acid aqueous solution, ethanol was evaporated. The resulting residue was mixed with 1N hydrochloric acid aqueous solution and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. By evaporating the solvent, 776.6 mg (quantitative) of the title compound was obtained as a crude product.

Workup

  1. customAfter neutralization with 1N hydrochloric acid aqueous solution, ethanol was evaporated
  2. additionThe resulting residue was mixed with 1N hydrochloric acid aqueous solution
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customBy evaporating the solvent, 776.6 mg (quantitative) of the title compound

Sources & evidence

ORD record
ord-b9fea32b6ec64ec3b502afaf45d01489
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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