Acetic Acid → 3-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

HRID 1901599Notes

Reaction equation

HRID 1901599 reaction equation
C(O)(=O)C.C(O)=O.[C:8]([O:12][C:13]([N:15]1[CH:19]([CH2:20][O:21][C:22]2[C:26]3[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=3[O:24][N:23]=2)[CH2:18][O:17]C1(C)C)=[O:14])([CH3:11])([CH3:10])[CH3:9]>O>[C:8]([O:12][C:13]([NH:15][CH:19]([CH2:18][OH:17])[CH2:20][O:21][C:22]1[C:26]2[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=2[O:24][N:23]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 284Formic AcidHCID 23368515HCID 23368515, compound

Product 1

HCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazoleYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 19 ml of acetic acid and 19 ml of formic acid is added 3.84 g of 3-[(3-tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methoxy]-5-chloro-1,2-benzoisoxazole at 20°-25° C., and they are subjected to reaction at the same temperature for one hour. Subsequently, the reaction mixture is poured into 190 ml of water and they are stirred at the same temperature for one hour. The crystals precipitated are collected by filtration, to obtain 2.78 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. customthey are subjected to reaction at the same temperature for one hour
  2. customThe crystals precipitated
  3. filtrationare collected by filtration

Sources & evidence

ORD record
ord-4dafc90ca39c4c1aa2ea43603de346ed
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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