Ammonia → HCID 23368381, compound

HRID 1901608Notes

Reaction equation

HRID 1901608 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].[C:24](=[O:29])=[N:25][C:26](Cl)=[O:27].CO.[NH3:32]>C(Cl)Cl.O>[NH:25]([C:24]([O:23][CH2:22][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[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:29])[C:26]([NH2:32])=[O:27]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 119708Isocyanatocarbonyl chlorideHCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 23368381HCID 23368381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

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. This solution is added to 10 ml of a methanol solution (8.0N) of ammonia at -20° C. over 20 minutes, and the temperature is elevated to 0° C., at which they are subjected to reaction for 30 minutes. Water is added to the reaction mixture, 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, to obtain 3-(3-ureidocarbonyloxy-2-tert-butoxycarbonylaminopropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. customis elevated to 0° C., at which they
  2. customare subjected to reaction for 30 minutes
  3. customthe organic layer is separated
  4. washThe separated organic layer is washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-cf243cba3d204ff8bcb18a3ccb284af1
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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