Potassium Carbonate → HCID 46867019, compound

HRID 2353125Notes

Reaction equation

HRID 2353125 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[O:25][N:24]=[C:23]([CH2:26]OS(C)(=O)=O)[CH:22]=1>CC#N.O>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:26][C:23]2[CH:22]=[C:21]([CH3:20])[O:25][N:24]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 57476926Methanesulfonic acid 5-methyl-isoxazol-3-ylmethyl ester

Product 1

HCID 46867019HCID 46867019, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-BOC-piperazine (300 mg) in MeCN (5 mL) was added potassium carbonate (289 mg) followed by methanesulfonic acid 5-methyl-isoxazol-3-ylmethyl ester (369 mg). The reaction mixture was heated to reflux for 24 h. After cooling the reaction mixture was diluted with water extracted into ethyl acetate, dried (MgSO4) and the solvent was removed in vacuo to yield 4-(5-methyl-isoxazol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (404 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted into ethyl acetate
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9c1ac4fe190e4f04a1f61b848aec38b8
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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