Hydrochloric Acid → HCID 21349882, compound

HRID 2186733Notes

Reaction equation

HRID 2186733 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][CH2:14][CH2:15][CH2:16][N:17]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27]C3CCCCO3)[C:21]=2[O:20][CH2:19][C:18]1=O)=O.Cl>CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:13][CH2:14][CH2:15][CH2:16][N:17]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([OH:27])[C:21]=2[O:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22448917HCID 22448917, compound

Product 1

HCID 21349882HCID 21349882, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-(2-naphthoylamino)propyl)-3-oxo-8-(tetrahydropyran-2-yloxy)-3,4-dihydro-2H-1,4-benzooxazine (398 mg) was dissolved in methanol (5 ml), and a 1N hydrochloric acid aqueous solution was added to the resultant solution, and the mixture was stirred at 0° C. for 1 hour. The reaction solution was extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was dissolved in THF (5 ml). A borane THF complex (1.0 M in THF, 2.8 ml) was added to the resultant solution, and then the mixture was refluxed under heating for 3.5 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, and then the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:7) to obtain the object compound (166 mg, yield 52%).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washthe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe resultant residue was dissolved in THF (5 ml)
  6. additionA borane THF complex (1.0 M in THF, 2.8 ml) was added to the resultant solution
  7. temperaturethe mixture was refluxed
  8. temperatureunder heating for 3.5 hours
  9. additionA saturated sodium bicarbonate aqueous solution was added to the reaction solution
  10. extractionthe mixture was then extracted with ethyl acetate
  11. washThe resultant organic layer was washed with saturated brine
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:7)

Sources & evidence

ORD record
ord-d0d7c279bc184b32ada0627ebe5efc13
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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