Sodium Hydroxide → HCID 57494065, compound

HRID 2403427Notes

Reaction equation

HRID 2403427 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]>O1CCOCC1.O.C(N(CC)CC)C>[C:14]([O:18][C:19]([N:6]1[CH2:7][CH2:8][N:3]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:4]([C:9]([OH:11])=[O:10])[CH2:5]1)=[O:21])([CH3:17])([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 90495Di-tert-butyl dicarbonateHCID 2723757Piperazine-2-carboxylic acid dihydrochloride

Product 1

HCID 57494065HCID 57494065, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of piperazine-2-carboxylic acid dihydrochloride (10 g) in 1,4-dioxane (100 mL) and water (50 mL) at 0° C. was added 17M NaOH solution in portions followed by di-tert-butyldicarbonate (11.8 g). The resulting mixture was warmed to R.T. and stirred for 5 h. Triethylamine (13.7 mL) and methanesulfonyl chloride (3.8 mL) were added this mixture was stirred overnight at R.T. The reaction mixture was concentrated in vacuo, diluted with 2M HCl and extracted with EtOAC. Combined extracts were dried (MgSO4), filtered and concentrated to give 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester (8.46 g).

Workup

  1. stirringwas stirred overnight at R.T
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with 2M HCl
  4. extractionextracted with EtOAC
  5. dry with materialCombined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-37ecc69abe114624b73cf485110ba095
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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