Hydrochloric Acid → HCID 23368426, compound

HRID 1901635Notes

Reaction equation

HRID 1901635 reaction equation
C(OC([NH:8][CH:9]([CH2:22][CH2:23][OH:24])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.ClS([N:29]=[C:30]=[O:31])(=O)=O.O.Cl>C(Cl)Cl.CO.CC(O)C>[ClH:21].[NH2:8][CH:9]([CH2:22][CH2:23][O:24][C:30](=[O:31])[NH2:29])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 23368550HCID 23368550, compound

Product 1

HCID 23368426HCID 23368426, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.67 g of 3-(2-tert-butoxycarbonylamino-4-hydroxybutoxy)-5-chloro-1,2-benzoisoxazole in 6 ml of methylene chloride is added 0.30 g of chlorosulfonyl isocyanate at -30° C., and the temperature is gradually elevated to 0° C., after which 5 ml of water is added and they are stirred for 30 minutes. The solvent is removed by distillation under reduced pressure, water and ethyl acetate are added to the residue obtained, and after shaking, 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 oily product obtained is dissolved in 8 ml of methanol, and thereto is added 1.5 ml of a 2-propanol solution (6.5M) of hydrogen chloride at room temperature, after which they are subjected to reaction at the same temperature for 18 hours. The crystals precipitated are collected by filtration, to obtain 0.29 g of colorless, crystalline 3-(2-amino-4-carbamoyloxybutoxy)-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 213.5°-215.5° C.

Workup

  1. customis gradually elevated to 0° C.
  2. customThe solvent is removed by distillation under reduced pressure, water and ethyl acetate
  3. additionare added to the residue
  4. customobtained
  5. stirringafter shaking
  6. customthe 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 oily product obtained
  11. customafter which they are subjected to reaction at the same temperature for 18 hours
  12. customThe crystals precipitated
  13. filtrationare collected by filtration

Sources & evidence

ORD record
ord-d3726f4ac56b4aea9df949f55dfaebd4
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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