Water → HCID 23368409, compound

HRID 1901626Notes

Reaction equation

HRID 1901626 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:24][OH:25])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([N:21]([CH3:23])[CH3:22])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:28]([N:30]=C=O)=[O:29].O>C(Cl)Cl>[C:28]([O:25][CH2:24][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]([N:21]([CH3:22])[CH3:23])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)(=[O:29])[NH2:30]

Participants

5

Reactant 3

HCID 962WaterHCID 76400Trichloroacetyl isocyanateHCID 23368483HCID 23368483, compound

Product 1

HCID 23368409HCID 23368409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.58 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-dimethylamino-1,2-benzoisoxazole in 12 ml of methylene chloride is added 0.26 g of trichloroacetyl isocyanate at -35° to -30° C., and the temperature is elevated to 0° C., after which they are subjected to reaction at the same temperature for one hour. To the reaction mixture is added 10 ml of water, and they are subjected to reaction at 20°-25° C. for one hour, after which the organic layer is separated. The separated organic layer is dried over anhydrous magnesium sulfate and thereafter the solvent is removed by distillation under reduced pressure, to obtain 0.94 g of brown, oily 3-(3-carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-dimethylamino-1,2-benzoisoxazole.

Workup

  1. customis elevated to 0° C.
  2. customafter which they are subjected to reaction at the same temperature for one hour
  3. customare subjected to reaction at 20°-25° C. for one hour
  4. customafter which the organic layer is separated
  5. dry with materialThe separated organic layer is dried over anhydrous magnesium sulfate
  6. customthe solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a347d9399aba4ac3bbb597da2ab5290b
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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