Benzyl Alcohol → HCID 86744594, compound

HRID 981285Notes

Reaction equation

HRID 981285 reaction equation
C([CH:4]1[CH2:6][CH:5]1[C:7]1[C:8]([F:27])=[CH:9][C:10]2[C:20](=[O:21])[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:12]3[C@@H:13]([CH3:17])[CH2:14][O:15][C:16]=1[C:11]=23)(O)=O.[C:28](Cl)(=[O:32])[O:29][CH2:30][CH3:31].[N-:34]=[N+]=[N-].[Na+].Cl.[CH2:39](O)[C:40]1C=C[CH:43]=[CH:42][CH:41]=1>CN(C)C=O.O1CCOCC1.O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:30]([O:29][C:28]([NH:34][CH:4]1[CH2:6][CH:5]1[C:7]1[C:8]([F:27])=[CH:9][C:10]2[C:20](=[O:21])[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:12]3[C@@H:13]([CH3:17])[CH2:14][O:15][C:16]=1[C:11]=23)=[O:32])[C:31]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

11

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 86744592HCID 86744592, compound

Product 1

HCID 86744594HCID 86744594, compoundYield 64%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

In 4 ml of N,N-dimethylformamide was suspended 200 mg of ethyl (S)-10-(2-carboxycyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylate. To the resulting suspension were added, with ice-cooling, 70 mg of ethyl chlorocarbonate and 65 mg of triethylamine. The resulting mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added 45 mg of sodium azide with ice-cooling. The resulting mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added 20 ml of chloroform and 20 ml of water in this order. 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, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. To the residue obtained were added 5 ml of dioxane and 115 mg of benzyl alcohol in this order. The resulting mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was purified by a column chromatography (eluant: chloroform/ethanol=15/1) to obtain 160 mg (yield: 64.0%) of ethyl (S)-10-(2-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6carboxylate.

Workup

  1. additionTo the resulting suspension were added, with ice-
  2. temperaturecooling
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred at the same temperature for 1 hour
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customTo the residue obtained
  10. stirringThe resulting mixture was stirred at 100° C. for 1.5 hours
  11. concentrationThe reaction mixture was concentrated under reduced pressure
  12. customThe residue obtained
  13. customwas purified by a column chromatography (eluant: chloroform/ethanol=15/1)

Sources & evidence

ORD record
ord-2d318ed7150645f8ac749a9255ca8ae1
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

Loading…