Hydrochloric Acid → HCID 17848805, compound

HRID 1766011Notes

Reaction equation

HRID 1766011 reaction equation
B.[CH2:2]1[CH2:6][O:5][CH2:4][CH2:3]1.Cl.[OH-].[Na+].C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28].[I-:31].[Na+].[CH2:33]1[CH2:37]OC[CH2:34]1>C(#N)C.CC(C)=O>[I:31][CH2:34][CH2:33][CH2:37][C:4]1[CH:3]=[CH:2][C:6]2[O:5][CH2:14][CH2:13][N:12]([S:27]([C:18]3[CH:19]=[CH:20][C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=3)(=[O:29])=[O:28])[C:15]=2[CH:16]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 71252-Naphthalenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 17848805HCID 17848805, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent2×

Procedure

1 N borane/THF solution (150 ml, 150 mmol) was added to a solution of methyl 3-(3,4-dihydro-2H-1,4-benzoxazine-3-oxo-6-yl)propionate (24 g, 102 mmol) obtained in 1) above in THF (400 ml) under cooling with ice-bath. The reaction solution was stirred overnight at room temperature, then 6 N hydrochloric acid (50 ml, 300 mmol) was added to the reaction solution which was then stirred for 2 hours, neutralized with 6 N aqueous sodium hydroxide and extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, dried over magnesium sulfate, and concentrated. After triethylamine (25 g, 250 mmol) was added to a solution of the residues in acetonitrile (300 ml), a solution of 2-naphthalene sulfonyl chloride (56 g, 250 mmol) in acetonitrile (100 ml) was added thereto under cooling with ice-bath and stirred at room temperature for 4 hours. The reaction solution was concentrated, and water was added to the residues which were then extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, dried over magnesium sulfate and concentrated. Sodium iodide (37.5 g, 250 mmol) was added to a solution of the residues in acetone (500 ml), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, and water (500 ml) was added to the concentrate which was then extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, dried over magnesium sulfate and concentrated, whereby the title compound (22 g) was obtained as powder.

Workup

  1. temperatureunder cooling with ice-bath
  2. stirringwas then stirred for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated saline solution, dried over magnesium sulfate
  6. concentrationconcentrated
  7. temperatureunder cooling with ice-bath
  8. stirringstirred at room temperature for 4 hours
  9. concentrationThe reaction solution was concentrated
  10. additionwater was added to the residues which
  11. extractionwere then extracted with ethyl acetate
  12. washThe extract was washed with water
  13. dry with materiala saturated saline solution, dried over magnesium sulfate
  14. concentrationconcentrated
  15. stirringthe mixture was stirred overnight at room temperature
  16. concentrationThe reaction solution was concentrated
  17. additionwater (500 ml) was added to the
  18. concentrationconcentrate which
  19. extractionwas then extracted with ethyl acetate
  20. washThe extract was washed with water
  21. dry with materiala saturated saline solution, dried over magnesium sulfate
  22. concentrationconcentrated

Sources & evidence

ORD record
ord-611160cac15c49a18b06d8a4e8c49fcf
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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