Water → HCID 68795638, compound

HRID 2065760Notes

Reaction equation

HRID 2065760 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].[Cl:18][C:19]1[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:17][O:16][C:14]([CH:13]1[CH2:12][N:11]([S:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[CH:20]=2)(=[O:27])=[O:26])[CH2:10][CH2:9][N:8]1[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 179093-Chlorobenzenesulphonyl chlorideHCID 27568181-(1,1-Dimethylethyl) 2-methyl 1,2-piperazinedicarboxylate

Product 1

HCID 68795638HCID 68795638, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-1-Boc-2-piperazinecarboxylic acid methyl ester (CAS Reg. No: [129799-15-1]) (1 g) in DMF (5 mL) was added 3-chlorobenzenesulfonyl chloride (0.95 g) and triethylamine (1.71 mL). The reaction mixture was stirred at RT overnight. Water was added and the mixture was extracted with ethyl acetate (×2). The combined organic layers were washed with water (×2) and brine, were dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, n-heptane/ethyl acetate 3:1) yielded 4-(3-chloro-benzenesulfonyl)-piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester as white foam (1.66 g), MS: 436.3 ([M+NH4, 1Cl]+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×2)
  2. washThe combined organic layers were washed with water (×2) and brine
  3. dry with materialwere dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (SiO2, n-heptane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-81592d984c374779b75845a54ce66ea6
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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