Water → HCID 23368484, compound

HRID 1901623Notes

Reaction equation

HRID 1901623 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:30][OH:31])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([N:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClS([N:36]=[C:37]=[O:38])(=O)=O.O>C(Cl)Cl>[C:37]([O:31][CH2:30][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([N:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)(=[O:38])[NH2:36]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 23368400HCID 23368400, compound

Product 1

HCID 23368484HCID 23368484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.11 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-(N-methyl-N-tert-butoxycarbonylamino)-1,2-benzoisoxazole in 5 ml of methylene chloride is added 0.10 g of chlorosulfonyl isocyanate at -45° to -40° 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 the solvent is then removed by distillation under reduced pressure, to obtain 0.10 g of yellow, oily 3-(3-carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-(N-methyl-N-tert-butoxycarbonylamino)-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 then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a755f03cd5ab4e3c877762ee8eaf0f57
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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