Dimethyl Sulfoxide → HCID 86625491, compound

HRID 2263056Notes

Reaction equation

HRID 2263056 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1[C:19]([CH3:20])=[C:18]([NH:21][C:22](=O)[O:23]CC(Cl)(Cl)Cl)[O:17][N:16]=1.CS(C)=O>O>[CH3:14][C:15]1[C:19]([CH3:20])=[C:18]([NH:21][C:22]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)=[O:23])[O:17][N:16]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

Product 1

HCID 86625491HCID 86625491, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)piperazine (5.00 g, 26.8 mmol), 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (3.85 g, 13.4 mmol), disopropylethylamine (2.33 ml, 13.4 mmol) and dimethylsulfoxide (50 ml) was stirred at 70° C. for 2 hours, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (1.80 g, 41.4%) as a solid.

Workup

  1. extractionthe mixture was extracted 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 recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-948d71e3f512499e8db760a0cceb3947
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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