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

HRID 1695013Notes

Reaction equation

HRID 1695013 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N@:13]1[CH2:15][CH:14]1[C@H:16]1[O:20][C:19](=[O:21])[C@H:18]([CH2:22][CH2:23][CH3:24])[CH2:17]1)(=[O:12])=[O:11])([O-:3])=[O:2].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][C:36]([CH3:39])([CH3:38])[NH:35][CH2:34][C:33]1=[O:40]>C1(C)C=CC=CC=1>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[C:33](=[O:40])[CH2:34][N:35]([CH2:15][C@H:14]([NH:13][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C@@H:16]2[CH2:17][C@@H:18]([CH2:22][CH2:23][CH3:24])[C:19](=[O:21])[O:20]2)[C:36]([CH3:39])([CH3:38])[CH2:37]1

Participants

4

Reactant 2

HCID 666457101-(2-Chlorophenyl)-5,5-dimethylpiperazin-2-oneHCID 178448141HCID 178448141, compound

Product 1

HCID 66645872N-{(S)-2-[4-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 700 mg of (3R,5S)-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]-3-propyldihydrofuran-2-one obtained in Example (116g) (1.98 mmol) and 611 mg of 1-(2-chlorophenyl)-5,5-dimethylpiperazin-2-one obtained in Example (1k) (2.57 mmol) in toluene (20 ml) was stirred at 110° C. for 1.5 hours. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone 5/1) to obtain 888 mg of the title compound (yield: 76%).

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: toluene/acetone 5/1)

Sources & evidence

ORD record
ord-ac758889021c49acace7d3a667b62076
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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