Benzyl Alcohol → HCID 10415367, compound

HRID 981291Notes

Reaction equation

HRID 981291 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:18][C:19]([NH:21][C:22]1([C:25]2[C:26]([F:44])=[C:27](F)[C:28]3[C:38](=[O:39])[C:37]([C:40]([OH:42])=[O:41])=[CH:36][N:30]4[CH:31]([CH3:35])[CH2:32][O:33][C:34]=2[C:29]=34)[CH2:24][CH2:23]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:1]([O:8][C:27]1[C:28]2[C:38](=[O:39])[C:37]([C:40]([OH:42])=[O:41])=[CH:36][N:30]3[CH:31]([CH3:35])[CH2:32][O:33][C:34]([C:29]=23)=[C:25]([C:22]2([NH:21][C:19]([O:18][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:20])[CH2:23][CH2:24]2)[C:26]=1[F:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10050381HCID 10050381, compound

Product 1

HCID 10415367HCID 10415367, compoundYield 24.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 2 ml of N,N-dimethylformamide was dissolved 230 mg of benzyl alcohol. To the resulting solution was added 85 mg of 60% sodium hydride with ice-cooling. The resulting mixture was stirred at room temperature for 30 minutes. Thereto was added, with ice-cooling, 250 mg of 10-(1-benzyloxycarbonylaminocyclopropyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid. The resulting mixture was stirred at room temperature for 7 hours. The reaction mixture was added to a mixture of 15 ml of ethyl acetate and 15 ml of water. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: chloroform/ethanol=10/1) to obtain 73.0 mg (yield: 24.6%) of 8-benzyloxy-10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid.

Workup

  1. temperaturecooling
  2. additionThereto was added, with ice-
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred at room temperature for 7 hours
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customThe residue obtained
  10. customwas purified by a column chromatography (eluant: chloroform/ethanol=10/1)

Sources & evidence

ORD record
ord-577c5a88b9a44101a1643fb3a7727677
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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