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

HRID 968470Notes

Reaction equation

HRID 968470 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)-propionateYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

43.5 g of tin-(II) chloride were added to a solution of 17.8 g of ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-{{3-{[(3-nitrophenyl)-sulfonyl]-amino}-phenyl}}-propanoate from Example II.2.e in 165 ml of ethanol, and the mixture was heated to reflux for a period of time of 2 h. The reaction mixture was hydrolized with 200 ml of aqueous 2N sodium hydroxide solution, then filtered through silica gel and washed with dichloromethane. The organic phase was dried over magnesium sulphate and concentrated to yield 9.2 g of a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for a period of time of 2 h
  3. filtrationfiltered through silica gel
  4. washwashed with dichloromethane
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67c4c1bf1eba46ac9556a04389c7aae6
Source dataset
uspto-grants-2007_12
Patent number
US07304037B2

Reaction notes

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