Sodium Hydroxide → Tert-butyl 4-[4-(4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

HRID 1744123Notes

Reaction equation

HRID 1744123 reaction equation
[Cl:1][C:2]([Cl:41])([Cl:40])[CH2:3][O:4][C:5]([N:7](C(OCC(Cl)(Cl)Cl)=O)[C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[N:10][O:11][N:12]=1)=[O:6].[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O>[Cl:40][C:2]([Cl:1])([Cl:41])[CH2:3][O:4][C:5]([NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)=[N:10][O:11][N:12]=1)=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22236059Tert-butyl 4-[4-(4-{bis[(2,2,2-trichloroethoxy)carbonyl]amino}-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

Product 1

HCID 22235984Tert-butyl 4-[4-(4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To tert-butyl 4-[4-(4-{bis[(2,2,2-trichloroethoxy)carbonyl]amino}-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate (1.21 g, 1.74 mmol) in THF (25 mL) was added an aqueous solution of NaOH (1.0 M, 4.0 mL, 4.0 mmol) dropwise and the reaction mixture was stirred for 1 hour. The reaction was poured into brine and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 3/7) to afford tert-butyl 4-[4-(4-{[(2,2,2-trichloroethoxy)carbonyl]amino}-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate.

Workup

  1. extractionthe product extracted with Et2O (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 3/7)

Sources & evidence

ORD record
ord-d3db46e00fab4a82a522dae933ee4dab
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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