Potassium tert-butoxide → HCID 14770861, compound

HRID 1090397Notes

Reaction equation

HRID 1090397 reaction equation
[C:1]([NH:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:29])[C:18](=[CH:24][NH:25][CH:26]3[CH2:28][CH2:27]3)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12](F)[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:1]([NH:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]3[C:13]([C:17](=[O:29])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][N:25]3[CH:26]3[CH2:28][CH2:27]3)=[CH:14][C:15]=2[F:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471863HCID 178471863, compound

Product 1

HCID 14770861HCID 14770861, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of 21.0 g (50 mmol) of 4-[3-(acetylamino) cyclopentyl]-α-[(cyclopropylamino)methylene]-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 50 ml of dry t-butanol. The resulting suspension was stirred and heated at 65° for 3 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 16.5 g of the title compound.

Workup

  1. temperatureheated at 65° for 3 hours
  2. customat room temperature
  3. customovernight
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washwashed with 1.0 M hydrochloric acid
  7. dry with materialAfter drying (MgSO4)
  8. customevaporating the solvent in vacuo
  9. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-339c397f48c0422aa3d1a244f45f0073
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

Loading…