Sodium Hydroxide → Ethyl 3-allyloxycarbonylamino-3-(3-aminophenyl)-propionate

HRID 968468Notes

Reaction equation

HRID 968468 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]([N+:24]([O-])=O)[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]([NH2:24])[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 21101502Ethyl 3-allyloxycarbonylamino-3-(3-nitrophenyl)-propionate

Product 1

HCID 21101501Ethyl 3-allyloxycarbonylamino-3-(3-aminophenyl)-propionateYield 76.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

64.6 g of tin-(II) chloride were added to a solution of 18.8 g of ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-(3-nitrophenyl)-propanoate from Example II.2.c in 245 ml of ethanol, and the mixture was heated to reflux for 2 h. The reaction mixture was hydrolized with 300 ml of aqueous 2N sodium hydroxide solution, then filtered through silica gel, and the filtrate was washed with dichloromethane. The organic phase was dried over magnesium sulphate and concentrated to yield 13.1 g of a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationfiltered through silica gel
  4. washthe filtrate was washed with dichloromethane
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-42f615a4b778435dbb31ca493940e88a
Source dataset
uspto-grants-2007_12
Patent number
US07304037B2

Reaction notes

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