Hydrochloric Acid → HCID 11097387, compound

HRID 1111048Notes

Reaction equation

HRID 1111048 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:16]([OH:18])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH:2]=[CH2:3].Cl.[C:20](=O)(O)[O-].[Na+]>CO>[CH3:20][O:17][C:16](=[O:18])[C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13968131N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine

Product 1

HCID 11097387HCID 11097387, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.06 mol of N-(allyloxycarbonyl)phenylalanine, prepared as described by H. Kunz and C. Unverzagt in Angew. Chem. Int. Ed. Engl., 1984, 23, 436-437, 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-(allyloxycarbonyl)phenylalanine 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-4434831815b34e9c92f94cafecba998e
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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