methyl 4-(4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)phenyl)-4-nitrobutanoate → N-(2,4-dimethylphenyl)-N-isobutyl-4-(5-oxopyrrolidin-2-yl)benzenesulfonamide

HRID 1487059Notes

Reaction equation

HRID 1487059 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([N+:26]([O-])=O)[CH2:20][CH2:21][C:22]([O:24]C)=O)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[H][H]>[Pd].C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:29][CH:30]([CH3:31])[CH3:32])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:20][CH2:21][C:22](=[O:24])[NH:26]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 89479545methyl 4-(4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)phenyl)-4-nitrobutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 89875685N-(2,4-dimethylphenyl)-N-isobutyl-4-(5-oxopyrrolidin-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of palladium on carbon (22.09 mg, 0.208 mmol) in ethanol (5 mL) stirred under nitrogen at room temperature was added a solution of methyl 4-(4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)phenyl)-4-nitrobutanoate (96 mg, 0.208 mmol) in ethanol (5 mL) dropwise. The flask was carefully filled with hydrogen and the reaction mixture was stirred at 20° C. for 2 hours. LCMS analysis showed disappearance of starting material. The reaction mixture was filtered through celite under an atmosphere of nitrogen and the filtrate evaporated in vacuo to give a yellow gum. The crude was purified by mass directed autoprep (formic acid modifier). The relevant fractions were concentrated under a stream of nitrogen to give the required product, 1.01 mg. LCMS [LCMS1] Rt 1.17 min, m/z (ES+) 400 (M+H, weak) 442 (M+MeCN+H)

Workup

  1. stirringthe reaction mixture was stirred at 20° C. for 2 hours
  2. filtrationThe reaction mixture was filtered through celite under an atmosphere of nitrogen
  3. customthe filtrate evaporated in vacuo
  4. customto give a yellow gum
  5. customThe crude was purified by mass
  6. concentrationThe relevant fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-7362a191376140f08a2f521adb1c0419
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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