Sodium Hydroxide → HCID 22388009, compound

HRID 1699807Notes

Reaction equation

HRID 1699807 reaction equation
C(OC([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[O:17][CH2:18][C:19]([CH3:22])([CH3:21])[N:20]=3)=[CH:13][CH:14]=2)[C:9]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[CH:8][CH:7]1P(OC)(OC)=O)=O)C.[OH-].[Na+]>C(O)C>[CH3:21][C:19]1([CH3:22])[CH2:18][O:17][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[N:6]=[CH:7][CH:8]=[C:9]3[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[N:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22388180HCID 22388180, compound

Product 1

HCID 22388009HCID 22388009, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-ethoxycarbonyl-6-(4,5-dihydro-4,4-dimethyloxazol-2-yl)-2-dimethoxyphosphoryl-4-(4-phenylbenzyl)-1,2-dihydroquinoline (738 mg), ethanol (20 ml) and 1N aqueous sodium hydroxide solution (4 ml) was refluxed under heating for 2 hr. The reaction mixture was concentrated to dryness under reduced pressure. Water was added and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed once with saturated brine, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give the objective compound (140 mg) as a white solid.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 2 hr
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. additionWater was added
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washwashed once with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-8ea46165533745b6b65cbc63ad92f143
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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