Sodium Hydroxide → HCID 14300213, compound

HRID 34714Notes

Reaction equation

HRID 34714 reaction equation
C([O:3][C:4]([C:6](=[CH2:25])[CH2:7][CH2:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH:13]1)=[O:11])=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:4]([C:6](=[CH2:25])[CH2:7][CH2:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[NH:13]1)=[O:11])([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14300211HCID 14300211, compound

Product 1

HCID 14300213HCID 14300213, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 8.2 g of tert.butyl 1-[5-(ethoxycarbonyl)-5-hexenoyl]-hexahydro-3-(S)-pyridazinecarboxylate in 25 ml of ethanol was treated with 23.7 ml of 1N aqueous sodium hydroxide solution for 16 hours. The solution was diluted with 80 ml of water and the volume was then reduced to 80 ml by evaporation. The solution was washed with diethyl ether and the pH of the aqueous solution was adjusted to 3 using 2N aqueous hydrochloric acid. The solution was then extracted with dichloromethane. The organic solution was evaporated and the residue was chromatographed on silica gel using dichloromethane/methanol (9:1) for the elution, whereby there were obtained 3.62 g of tert.butyl 1-[5-(carboxy)-5-hexenoyl]-hexahydro-3(S)-pyridazinecarboxylate in the form of a white solid of melting point 86°-88° C., from n-hexane.

Workup

  1. customthe volume was then reduced to 80 ml by evaporation
  2. washThe solution was washed with diethyl ether
  3. extractionThe solution was then extracted with dichloromethane
  4. customThe organic solution was evaporated
  5. customthe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-c803efe484f642cca342c189331414d3
Source dataset
uspto-grants-1988_08
Patent number
US04762924

Reaction notes

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