Water → HCID 23368486, compound

HRID 1901611Notes

Reaction equation

HRID 1901611 reaction equation
[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]=[C:26]=[O:27].O.C(OCC)(=O)C>CN(C)C=O.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][O:23][C:26]([NH:25][CH3:24])=[O:27])[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:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12228Methyl IsocyanateHCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 23368486HCID 23368486, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.50 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole in 5 ml of N,N-dimethylformamide is added 0.14 g of cuprous chloride. To this solution is added a solution of 0.13 g of methyl isocyanate in 5 ml of methylene chloride at 20°-25° C., and they are further subjected to reaction at the same temperature for 30 minutes. Water and ethyl acetate are added to the reaction mixture, and after shaking, the organic layer is separated. The separated organic layer is washed with water and a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure, to obtain 3-(2-tert-butoxycarbonylamino-3-methylaminocarbonyloxypropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. customthey are further subjected to reaction at the same temperature for 30 minutes
  2. customthe organic layer is separated
  3. washThe separated organic layer is washed with water
  4. dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
  5. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4906bb6f3de74eb9b6fc5a1817adbd65
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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