5,5-Dimethyl-1-(2-methylphenyl)piperazin-2-one → N-{(S)-2-[2,2-Dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1695001Notes

Reaction equation

HRID 1695001 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].[CH3:24][C:25]1([CH3:39])[CH2:30][N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[C:28](=[O:38])[CH2:27][NH:26]1>C1(C)C=CC=CC=1>[CH3:24][C:25]1([CH3:39])[CH2:30][N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[C:28](=[O:38])[CH2:27][N:26]1[CH2:10][C@H:8]([NH:9][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[C@@H:6]1[CH2:7][C@@H:3]([CH2:1][CH3:2])[C:4](=[O:23])[O:5]1

Participants

4

Reactant 2

HCID 666459595,5-Dimethyl-1-(2-methylphenyl)piperazin-2-oneHCID 178455819HCID 178455819, compound

Product 1

HCID 66645655N-{(S)-2-[2,2-Dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 770 mg of (3R,5S)-3-ethyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (106g) (2.26 mmol) and 593 mg of 5,5-dimethyl-1-(2-methylphenyl)piperazin-2-one obtained in Example (51d) (2.71 mmol) in toluene (23 ml) was stirred at 110° C. for five 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=4/1) to obtain 1.22 g of the title compound (yield: 97%).

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=4/1)

Sources & evidence

ORD record
ord-421d7f98bdf34480800aac003e985e7a
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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