Hydrochloric Acid → HCID 23368390, compound

HRID 1901610Notes

Reaction equation

HRID 1901610 reaction equation
C(OC([NH:8][CH:9]([CH2:22][OH:23])[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.[C:24](=[O:29])=[N:25][C:26](Cl)=[O:27].Cl.[C:31](=O)([O-])[OH:32].[Na+]>C(Cl)Cl.C(OCC)(=O)C.CC(O)C.CO>[ClH:21].[NH2:8][CH:9]([CH2:22][O:23][C:24]([NH:25][C:26]([O:32][CH3:31])=[O:27])=[O: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

9

Reactant 4

HCID 313Hydrochloric AcidHCID 119708Isocyanatocarbonyl chlorideHCID 516892Sodium BicarbonateHCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 23368390HCID 23368390, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.00 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole in 5 ml of methylene chloride is added to a solution of 0.31 g of N-(chlorocarbonyl) isocyanate in 10 ml of methylene chloride at -50° to -40° C. To this solution is added 10 ml of methanol at -40° C., and the temperature is elevated to 0° C., at which they are subjected to reaction for 30 minutes. The solvent is removed from the reaction mixture by distillation under reduced pressure, and to the residue obtained is added 12.8 ml of a 2-propanol solution (7.5N) of hydrogen chloride, after which they are subjected to reaction at 20°-25° C. for 30 minutes. The solvent is removed from the reaction mixture by distillation under reduced pressure. To the residue obtained are added ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution, 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 9.6 ml of a 2-propanol solution (7.5N) of hydrogen chloride is added. The crystals obtained are collected by filtration, to obtain 0.42 g of colorless, crystalline 3-(2-amino-3-methoxycarbonylaminocarbonyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 184°-185° C.

Workup

  1. customis elevated to 0° C., at which they
  2. customare subjected to reaction for 30 minutes
  3. customThe solvent is removed from the reaction mixture by distillation under reduced pressure
  4. customto the residue obtained
  5. customafter which they are subjected to reaction at 20°-25° C. for 30 minutes
  6. customThe solvent is removed from the reaction mixture by distillation under reduced pressure
  7. customTo the residue obtained
  8. customthe organic layer is separated
  9. washThe separated organic layer is washed with a saturated saline solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. additionafter which 9.6 ml of a 2-propanol solution (7.5N) of hydrogen chloride is added
  12. customThe crystals obtained
  13. filtrationare collected by filtration

Sources & evidence

ORD record
ord-c76eab6cfaa945829f25633827bbde42
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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