Potassium tert-butoxide → HCID 14770828, compound

HRID 1090403Notes

Reaction equation

HRID 1090403 reaction equation
[C:1]([N:4]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][CH2:5]1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:1]([N:4]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][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471866HCID 178471866, compound

Product 1

HCID 14770828HCID 14770828, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 3.49 g (8.30 mmol) ethyl 4-(1-acetyl-4-piperidinyl)-α-[(cyclopropylamino)methylene]-2,5-difluoro-β-oxobenzenepropionate in 35 ml of t-butyl alcohol was treated with 0.93 g (8.30 mmol) potassium t-butoxide and stirred in an oil bath at 65° for 1.5 hours. The mixture was evaporated under vacuum and the residue extracted with 0.5 N hydrochloric acid. The organic layer was dried (MgSO4) and evaporated. The title compound was isolated by chromatography on silica gel and crystallization from toluene, mp 195°-201° C.

Workup

  1. customThe mixture was evaporated under vacuum
  2. extractionthe residue extracted with 0.5 N hydrochloric acid
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-bce2c3cc066f4cd18d969d3fe43daa80
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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