Hydrochloric Acid → HCID 23368483, compound

HRID 1901625Notes

Reaction equation

HRID 1901625 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][OH:14])[C:6]=2[CH:23]=1.Cl.[CH2:25]=O.[C:27]([BH3-])#[N:28].[Na+].[OH-].[Na+]>CO.O.C(OCC)(=O)C.O1CCOCC1>[C:19]([O:18][C:16]([NH:15][CH:12]([CH2:13][OH:14])[CH2:11][O:10][C:7]1[C:6]2[CH:23]=[C:2]([N:28]([CH3:27])[CH3:25])[CH:3]=[CH:4][C:5]=2[O:9][N:8]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 23368500HCID 23368500, compound

Product 1

HCID 23368483HCID 23368483, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.61 g of 5-amino-3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 18 ml of methanol are added 1.3 ml of a dioxane solution (2.2N) of hydrogen chloride and 0.49 g of 37% formalin at 20°-25° C., and then, 0.19 g of sodium cyanoborohydride is added at 15°-20° C., after which they are subjected to reaction at the same temperature for 30 minutes. Ethyl acetate and water are added to the reaction mixture and the pH is adjusted to 10 with an 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 residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=3:2], to obtain 0.60 g of brown, oily 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-dimethylamino-1,2-benzoisoxazole.

Workup

  1. customafter which they are subjected to reaction at the same temperature for 30 minutes
  2. customafter which the organic layer is separated
  3. washThe separated organic layer is washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent is removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customis purified by a column chromatography [eluant:n-hexane:ethyl acetate=3:2]

Sources & evidence

ORD record
ord-adab1b44021647229584f0e4f8366af5
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

Loading…