Hydrochloric Acid → HCID 23368363, compound

HRID 1901604Notes

Reaction equation

HRID 1901604 reaction equation
[C:1]([O:4][CH2:5][CH:6]([NH:19]C(OC(C)(C)C)=O)[CH2:7][O:8][C:9]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[O:11][N:10]=1)(=[O:3])[NH2:2].Cl.O1CCOCC1>C(Cl)(Cl)Cl.CO.C(O)C>[ClH:18].[NH2:19][CH:6]([CH2:5][O:4][C:1](=[O:3])[NH2:2])[CH2:7][O:8][C:9]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[O:11][N:10]=1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 233685643-(3-Carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 23368363HCID 23368363, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 3.28 g of 3-(3-carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-chloro-1,2-benzoisoxazole in 33 ml of chloroform and 33 ml of methanol is added 7.1 ml of conc hydrochloric acid at 20°-25° C., and they are subjected to reaction at the same temperature overnight. The solvent is removed from the reaction mixture by distillation under reduced pressure, and ethyl acetate and water are added to the residue obtained. After shaking, the aqueous layer is separated. To the separated aqueous layer is again added ethyl acetate, and the pH is adjusted to 10 with a 10% (w/w) aqueous sodium hydroxide solution, after which the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The crystals obtained are dissolved in 66 ml of ethanol, and to this solution is added 4.5 ml of a dioxane solution (2.2N) of hydrogen chloride at 20°-25° C., after which the crystals precipitated are collected by filtration, to obtain 2.16 g of colorless, crystalline 3-(2-amino-3-carbamoyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 215°-216° C.

Workup

  1. customthey are subjected to reaction at the same temperature overnight
  2. customThe solvent is removed from the reaction mixture by distillation under reduced pressure, and ethyl acetate and water
  3. additionare added to the residue
  4. customobtained
  5. customthe aqueous layer is separated
  6. customafter which the organic layer is separated
  7. washThe separated organic layer is washed with a saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent is removed by distillation under reduced pressure
  10. customThe crystals obtained
  11. customafter which the crystals precipitated
  12. filtrationare collected by filtration

Sources & evidence

ORD record
ord-bec9c153bf0840ac83bc310876d457f9
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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