Hydrochloric Acid → HCID 54054013, compound

HRID 1111044Notes

Reaction equation

HRID 1111044 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[CH:2]=[CH2:3].Cl.[C:17](=O)(O)[O-].[Na+]>CO>[CH3:17][O:14][C:13](=[O:15])[C@H:11]([CH3:12])[NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53702760N-[2-(Prop-2-en-1-yl)phenyl]-L-alanine

Product 1

HCID 54054013HCID 54054013, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.06 mol of N-(2-allylphenyl)alanine, prepared as described by A. Padwa, H. L. Gingrich, and R. Lim in J. Org. Chem.,1982, 47, 2447-2456, and 0.066 mol of HCl in 100 mL of CH3OH is stirred at reflux for 8 hours. The solution is then cooled and treated with 0.066 mol of sodium bicarbonate. The solvent is removed by rotary evaporator, and the residue is dissolved in diethyl ether, filtered, dried over MgSO4, and filtered. The solvent is removed by rotary evaporator to give N-(2-allylphenyl)alanine methyl ester.

Workup

  1. temperatureat reflux for 8 hours
  2. temperatureThe solution is then cooled
  3. customThe solvent is removed by rotary evaporator
  4. dissolutionthe residue is dissolved in diethyl ether
  5. filtrationfiltered
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-e11f90504d1f423caf46760b252eb68d
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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