Potassium tert-butoxide → HCID 14770862, compound

HRID 1090399Notes

Reaction equation

HRID 1090399 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:30])[C:13]2[CH:18]=[C:17]([F:19])[C:16]([CH:20]3[CH2:28][CH2:27][C:22]4([O:26][CH2:25][CH2:24][O:23]4)[CH2:21]3)=[CH:15][C:14]=2F)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[O:26]1[C:22]2([CH2:27][CH2:28][CH:20]([C:16]3[CH:15]=[C:14]4[C:13]([C:12](=[O:30])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]4[CH:1]4[CH2:3][CH2:2]4)=[CH:18][C:17]=3[F:19])[CH2:21]2)[O:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471862HCID 178471862, compound

Product 1

HCID 14770862HCID 14770862, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of 21.4 g (50 mmol) of α-[(cyclopropylamino) methylene]-4-(1,4-dioxaspiro[4.4]non-7-yl)-2,5-difluoro-β-oxobenzenepropanoic acid, ethyl ester in 250 ml of dry t-butanol was treated with a slurry of 6.2 g (55 mmol) of potassium t-butoxide in 150 ml of dry t-butanol. The resulting suspension was stirred at 65° for 4 hours and then at room temperature overnight. The solvent was removed in vacuo and the residue was dissolved in methylene chloride and washed with 1.0 M hydrochloric acid. After drying (MgSO4) and evaporating the solvent in vacuo, the residue was recrystallized from ethyl acetate/hexane to give 17.3 g of the title compound.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with 1.0 M hydrochloric acid
  6. dry with materialAfter drying (MgSO4)
  7. customevaporating the solvent in vacuo
  8. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-40e239f3a4a44f65b90c8da6eadacf73
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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