Ethanol → HCID 23019672, compound

HRID 1354201Notes

Reaction equation

HRID 1354201 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7](=[O:28])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[S:16][C:17](OC4CCCCO4)=[C:18]([F:20])[CH:19]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.[CH2:34]([OH:36])C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7](=[O:28])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[S:16][C:17]([CH2:34][OH:36])=[C:18]([F:20])[CH:19]=2)[CH:10]=[CH:9]3)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 23019674HCID 23019674, compound

Product 1

HCID 23019672HCID 23019672, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

318 mg of ethyl 1-cyclopropyl-8-[4-fluoro-5-(tetrahydropyran-2-yloxy)-thiophen-2-yl]-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 101) was dissolved in 5 ml of tetrahydrofuran. 5 ml of ethanol and 43.0 mg of pyridinium p-toluenesulfonate were added to the obtained solution, and they were heated under reflux for 3 hours. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution. After the extraction with ethyl acetate, the organic layer was washed with water and then with saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by the silica gel column chromatography (eluent: chloroform/ethyl acetate=5/1) to obtain 230 mg of ethyl 1-cyclopropyl-8-(4-fluoro-5-hydroxymethylthiophen-2-yl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 3 hours
  3. extractionAfter the extraction with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialwith saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by the silica gel column chromatography (eluent: chloroform/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e93a82666a9547c1a78128c799b99b1a
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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