Ethyl Acetate → HCID 19919495, compound

HRID 1975694Notes

Reaction equation

HRID 1975694 reaction equation
[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][CH:17]3[S:20][C:21](=[O:23])[CH:22]=[C:16]3[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[C:26](Cl)(=[O:35])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(OCC)(=O)C>CN(C)C=O>[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][C:17]3[S:20][C:21]([O:23][C:26](=[O:35])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][C:16]=3[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69819Nonanoyl chlorideHCID 114162775-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

Product 1

HCID 19919495HCID 19919495, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g (3.0 mmole) of 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine (prepared as described in Example 20) was dissolved in 15 ml of dimethylformamide, and then 0.18 g (4.5 mmole) of a 60% w/w dispersion of sodium hydride in mineral oil and 0.82 ml (4.5 mmole) of nonanoyl chloride were added, in that order, to the resulting mixture, whilst ice-cooling. The resulting reaction mixture was then stirred at the same temperature for 30 minutes, after which it was stirred at room temperature for a further 5 hours. 300 ml of ethyl acetate were then added to the mixture, which was then washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography, using a 100:2 by volume mixture of toluene and ethyl acetate as the eluent, to give a yellow oil. The oil was crystallized from petroleum ether to obtain the title compound as white crystals, melting at 45°-48° C., in a yield of 40%.

Workup

  1. temperaturecooling
  2. customThe resulting reaction mixture
  3. stirringafter which it was stirred at room temperature for a further 5 hours
  4. washwas then washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed by evaporation under reduced pressure
  8. additionby volume mixture of toluene and ethyl acetate as the eluent
  9. customto give a yellow oil
  10. customThe oil was crystallized from petroleum ether

Sources & evidence

ORD record
ord-af35517e089b4bb881119643afe111e6
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

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