Methyl iodide → HCID 57494066, compound

HRID 1689922Notes

Reaction equation

HRID 1689922 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([OH:11])=[O:10].[OH-].[Na+].[C:14]([O:18][C:19]([O:21]C(OC(C)(C)C)=O)=O)([CH3:17])([CH3:16])[CH3:15].[CH3:29][S:30](Cl)(=[O:32])=[O:31].[C:34](=O)([O-])[O-].[K+].[K+].IC>O1CCOCC1.O.CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:34][O:10][C:9]([CH:4]1[N:3]([S:30]([CH3:29])(=[O:32])=[O:31])[CH2:8][CH2:7][N:6]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:21])[CH2:5]1)=[O:11]

Participants

12

Reactant 6

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 90495Di-tert-butyl dicarbonateHCID 2723757Piperazine-2-carboxylic acid dihydrochloride

Product 1

HCID 57494066HCID 57494066, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Amine preparation: To a suspension of piperazine-2-carboxylic acid dihydrochloride (10.0 g) in 1,4-dioxane (100 mL) and water (50 mL), cooled down to 0° C., was slowly added 17M sodium hydroxide solution (8.6 mL) followed by di-tert-butyldicarbonate (11.8 g). The reaction mixture was warmed to room temperature and stirred for 5 h. Triethylamine (13.7 mL) followed by methanesulfonyl chloride (3.8 mL) was then added. After stirring for 24 h the reaction mixture was concentrated down, the residue diluted with ethyl acetate, washed with 2M hydrochloric acid, brine, dried (MgSO4) and the solvent removed in vacuo to yield crude 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tent-butyl ester (8.46 g). This was subsequently dissolved in DMF (50 mL), and was treated with added potassium carbonate (7.5 g) and iodomethane (8.5 mL). After stirring for 24 h the reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (3.27 g).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. additionwas then added
  3. stirringAfter stirring for 24 h the reaction mixture
  4. concentrationwas concentrated down
  5. additionthe residue diluted with ethyl acetate
  6. washwashed with 2M hydrochloric acid, brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customto yield crude 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tent-butyl ester (8.46 g)
  10. stirringAfter stirring for 24 h the reaction mixture
  11. washwashed with water, brine
  12. dry with materialdried (MgSO4)
  13. customthe solvent removed in vacuo
  14. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-536b75f78ea94e3cb128a6e1ab9ac735
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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