Sodium Hydroxide → Ethyl 3-allyloxycarbonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionate

HRID 1353035Notes

Reaction equation

HRID 1353035 reaction equation
[Sn](Cl)Cl.[CH2:4]([O:7][C:8]([NH:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=2)(=[O:27])=[O:26])[CH:19]=1)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH:5]=[CH2:6].[OH-].[Na+]>C(O)C>[CH2:4]([O:7][C:8]([NH:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=2)(=[O:27])=[O:26])[CH:19]=1)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 21101499Ethyl 3-allyloxycarbonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

Product 1

HCID 21101498Ethyl 3-allyloxycarbonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride (39.7 g) was added to a solution of ethyl 3-allyloxycarbonylamino-3(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate from II.1e (16.8 g) in 155 ml of ethanol and the reaction mixture was heated under reflux for 2 h. After cooling, the solution was adjusted to pH=7 using 2N NaOH, briefly heated, cooled again and filtered. It was then extracted with dichloromethane, and the org. phase was dried (MgSO4) and concentrated. 7.3 g of product were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. temperaturebriefly heated
  5. temperaturecooled again
  6. filtrationfiltered
  7. extractionIt was then extracted with dichloromethane
  8. dry with materialphase was dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a9c650e6c3e24ed7837cdac0f70a8a45
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

Loading…