Stannous Chloride → Ethyl 3-(3-aminophenyl)-3-benzenesulphonylamino-propionate

HRID 1353040Notes

Reaction equation

HRID 1353040 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]([N+:27]([O-])=O)[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]([NH2:27])[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 11188106Ethyl 3-benzenesulphonylamino3-(3-nitrophenyl)-propionate

Product 1

HCID 15907252Ethyl 3-(3-aminophenyl)-3-benzenesulphonylamino-propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride (4.77 g) was added to a solution of ethyl 3-benzenesulphonylamino3-(3-nitrophenyl)-propionate from II.4a (2.0 g) in 60 ml of ethanol and the reaction mixture was heated under reflux for 2 h. After cooling, the solution was hydrolysed on ice and an NaHCO3 solution (5%) was added to pH=8. The mixture was then extracted with dichloromethane, and the org. phase was washed with NaCl, dried (MgSO4) and concentrated. A yellow oil was obtained (yield: 1.79 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. extractionThe mixture was then extracted with dichloromethane
  5. washphase was washed with NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customA yellow oil was obtained (yield: 1.79 g)

Sources & evidence

ORD record
ord-d4b2c6b7ec0e455691e3d16c4fdefc48
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

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