Methanesulfonyl chloride → 1-(1,1-Dimethylethyl) 4-(methylsulfonyl)-1,2-piperazinedicarboxylate

HRID 1991411Notes

Reaction equation

HRID 1991411 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].CCN(C(C)C)C(C)C.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>C(Cl)Cl>[C:14]([O:13][C:11]([N:6]1[CH2:7][CH2:8][N:9]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:10][CH:5]1[C:3]([OH:2])=[O:4])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27568181-(1,1-Dimethylethyl) 2-methyl 1,2-piperazinedicarboxylate

Product 1

HCID 183875151-(1,1-Dimethylethyl) 4-(methylsulfonyl)-1,2-piperazinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mmol of Piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester were dissolved in 20 ml methylenchloride. 1.05 eq of DIPEA and mesylchloride were added. The reaction mixture was stirred at room temperature for 30 min. The product was extracted from etylacetate/water. The crude material was redissolved in methanol and treated with 2N NaOH. The reaction mixture was stirred at room temperature for 2 h. The mixture was neutralized with HCl and the product isolated via extraction from ethylacetate/water.

Workup

  1. extractionThe product was extracted from etylacetate/water
  2. dissolutionThe crude material was redissolved in methanol
  3. additiontreated with 2N NaOH
  4. stirringThe reaction mixture was stirred at room temperature for 2 h
  5. customthe product isolated via extraction from ethylacetate/water

Sources & evidence

ORD record
ord-e06f2204c8154ccbbb60379ff8c3e963
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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