Water → 3-(3-Carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-chloro-1,2-benzoisoxazole

HRID 1901603Notes

Reaction equation

HRID 1901603 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].ClS([N:28]=[C:29]=[O:30])(=O)=O.O>C(Cl)Cl>[C:29]([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:30])[NH2:28]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 233685643-(3-Carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-chloro-1,2-benzoisoxazoleYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3.43 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole in 34 ml of methylene chloride is added 1.70 g of chlorosulfonyl isocyanate at -45° to -40° C., and the temperature thereof 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 methylene chloride is removed by distillation under reduced pressure. The crystals obtained are collected by filtration, to obtain 3.30 g of 3-(3-carbamoyloxy-2-tert-butoxycarbonylaminopropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. customthereof is 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 methylene chloride is removed by distillation under reduced pressure
  5. customThe crystals obtained
  6. filtrationare collected by filtration

Sources & evidence

ORD record
ord-6c0cf16dae814ead89507946b2d0d23f
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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