Water → HCID 23368512, compound

HRID 1901618Notes

Reaction equation

HRID 1901618 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][N:15]=[C:14]([O:17][CH2:18][CH:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][OH:21])[C:13]=2[CH:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClS([N:35]=[C:36]=[O:37])(=O)=O.O>C(Cl)Cl>[C:36]([O:21][CH2:20][CH:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][O:17][C:14]1[C:13]2[CH:30]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH:10]=[CH:11][C:12]=2[O:16][N:15]=1)(=[O:37])[NH2:35]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 23368467HCID 23368467, compound

Product 1

HCID 23368512HCID 23368512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.47 g of 5-tert-butoxycarbonylamino-3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 10 ml of methylene chloride is added 0.21 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. Subsequently, 10 ml of water is added, and they are subjected to reaction at 20°-25° C. for one hour. The solvent is removed from the reaction mixture by distillation under reduced pressure, and the crystals obtained are collected by filtration, to obtain 0.47 g of colorless, crystalline 3-(3-carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-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. customthey are subjected to reaction at 20°-25° C. for one hour
  4. customThe solvent is removed from the reaction mixture by distillation under reduced pressure
  5. customthe crystals obtained
  6. filtrationare collected by filtration

Sources & evidence

ORD record
ord-4ff326cd461d4e35ae94b190955f934b
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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