Potassium tert-butoxide → HCID 14770829, compound

HRID 1090410Notes

Reaction equation

HRID 1090410 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]=[C: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][CH2:5]1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:1]([N:4]1[CH2:9][CH:8]=[C: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][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471865HCID 178471865, compound

Product 1

HCID 14770829HCID 14770829, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 4.70 g (11.3 mmol) of ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridyl)-α-[(cyclopropylamino) methylene]-2,5-difluoro-β-oxobenzenepropionate in 35 ml of t-butyl alcohol was treated with 1.26 g (11.3 mmol) potassium t-butoxide and stirred in an oil bath at 65° C. for 5.5 hours. The mixture was evaporated under vacuum and the residue was dissolved in chloroform and extracted with 0.5 N hydrochloric acid. The organic layer was dried (MgSO4), evaporated and the title compound purified by chromatograph on silica gel and crystallization from toluene, mp 190°-192° C.

Workup

  1. customThe mixture was evaporated under vacuum
  2. dissolutionthe residue was dissolved in chloroform
  3. extractionextracted with 0.5 N hydrochloric acid
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe title compound purified by chromatograph on silica gel and crystallization from toluene, mp 190°-192° C.

Sources & evidence

ORD record
ord-1c53506c223a46ad92795a11d265dd16
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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