1-(2-Chlorophenyl)-5,5-dimethylpiperazin-2-one → N-{(S)-2-[4-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694995Notes

Reaction equation

HRID 1694995 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][C@@H:6]([CH:8]2[CH2:10][N@@:9]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[O:5][C:4]1=[O:23])[CH3:2].[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][CH2:33][C:32]1=[O:39]>C1(C)C=CC=CC=1>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[C:32](=[O:39])[CH2:33][N:34]([CH2:10][C@H:8]([NH:9][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[C@@H:6]2[CH2:7][C@@H:3]([CH2:1][CH3:2])[C:4](=[O:23])[O:5]2)[C:35]([CH3:38])([CH3:37])[CH2:36]1

Participants

4

Reactant 2

HCID 666457101-(2-Chlorophenyl)-5,5-dimethylpiperazin-2-oneHCID 178455819HCID 178455819, compound

Product 1

HCID 66645496N-{(S)-2-[4-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 916 mg of (3R,5S)-3-ethyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (106g) (2.69 mmol) and 771 mg of 1-(2-chlorophenyl)-5,5-dimethylpiperazin-2-one obtained in Example (1k) (3.23 mmol) in toluene (27 ml) was stirred at 110° C. for two hours. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/ethyl acetate=3/1-2/1) to obtain 1.49 g of the title compound (yield: 96%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/ethyl acetate=3/1-2/1)

Sources & evidence

ORD record
ord-7130798d7bf540c7868e6fa2ff2afde9
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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