Water → HCID 86750033, compound

HRID 1901655Notes

Reaction equation

HRID 1901655 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][OH:14])[C:6]=2[CH:23]=1.C(N(CC)CC)C.[CH3:31][N:32]=[C:33]=[S:34].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:13][O:14][C:33](=[S:34])[NH:32][CH3:31])[C:6]=2[CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 233683553-(2-Tert-butoxycarbonylamino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 86750033HCID 86750033, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.8 g of 5-chloro-3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 8 ml of N,N-dimethylformamide are added 1.6 ml of triethylamine and 0.51 g of methyl isothiocyanate at room temperature, and they are subjected to reaction at 110° C. for four hours. After cooling, water and ethyl acetate are added to the reaction mixture, they are shaken and the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a silica gel column chromatography [eluant:toluene:ethyl acetate=5:1], to obtain 0.4 g of brown, solid 5-chloro-3-(2-tert-butoxy carbonylamino-3-methylthiocarbamoyloxypropoxy)-1,2-benzoisoxazole.

Workup

  1. customthey are subjected to reaction at 110° C. for four hours
  2. temperatureAfter cooling
  3. customthe organic layer is separated
  4. washThe separated organic layer is washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent is removed by distillation under reduced pressure
  7. customThe residue obtained
  8. customis purified by a silica gel column chromatography [eluant:toluene:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-f29c21f4e75e4028930e6bbb7015e9ef
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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