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

HRID 1353033Notes

Reaction equation

HRID 1353033 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)-propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride (64.6 g) was added to a solution of ethyl 3-allyloxycarbonylamino-3-(3-nitrophenyl)-propionate from II.1c (18.8 g) in 245 ml of ethanol, and the reaction mixture was heated under reflux for 2 h. After cooling the solution, it 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. 10.9 g of product were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling the solution, it
  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-327cddf2a9414ccfa73b9ec2c93723bb
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

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