Stannous Chloride → Ethyl 3-benzenesulphonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionate

HRID 1353041Notes

Reaction equation

HRID 1353041 reaction equation
[Sn](Cl)Cl.[C:4]1([S:10]([NH:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-])=O)[CH:32]=3)(=[O:30])=[O:29])[CH:22]=2)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>C(O)C>[C:4]1([S:10]([NH:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=3)(=[O:29])=[O:30])[CH:22]=2)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:11])=[O:12])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 11421258Ethyl 3-benzenesulphonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

Product 1

HCID 15907253Ethyl 3-benzenesulphonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride (1.27 g) was added to a solution of ethyl 3-benzenesulphonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate from II.4c (600 mg) in 9 ml of ethanol, and the reaction mixture was heated under reflux for 2 h. After cooling, the solution was hydrolysed on ice and neutralized (pH=8) using NaHCO3 solution (5%). It was then extracted with dichloromethane, and the organic phase was washed with NaCl, dried (MgSO4) and concentrated. A yellow, viscous residue was obtained (yield: 394 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. extractionIt was then extracted with dichloromethane
  5. washthe organic phase was washed with NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customA yellow, viscous residue was obtained (yield: 394 mg)

Sources & evidence

ORD record
ord-847647facb654418a5d434ea5241c49c
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

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