Water → 4-(Benzo[d]isoxazol-3-ylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2262874Notes

Reaction equation

HRID 2262874 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]([C:19]([O:21]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O)=[N:2]1.C(N(C(C)C)CC)(C)C.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].O>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:19]([N:46]2[CH2:45][CH2:44][N:43]([C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:42])[CH2:48][CH2:47]2)=[O:21])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

Product 1

HCID 687244984-(Benzo[d]isoxazol-3-ylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl esterYield 33.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate (3.00 g, 6.19 mmol), diisopropylethylamine (1.08 ml, 6.19 mmol) and 1-(tert-butoxycarbonyl)piperazine (2.30 g, 12.4 mmol) in dimethyl sulfoxide (20 ml) was stirred at 70° C. for 2 hours. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was crystallized from hexane, which was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and then recrystallized from a mixed solvent of hexane and ethyl acetate to give 710 mg (33.2%) of the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was crystallized from hexane, which
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  7. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-aae8247b278b48bab8dc9e014726dfba
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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