Hydrochloric Acid → N-(allyloxycarbonyl)glycine methyl ester

HRID 1607855Notes

Reaction equation

HRID 1607855 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH:2]=[CH2:3].Cl.[C:13](=O)(O)[O-].[Na+]>CO>[CH3:13][O:10][C:9](=[O:11])[CH2:8][NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11964402N-[(allyloxy)carbonyl]glycine

Product 1

HCID 22154858N-(allyloxycarbonyl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.06 mol of N-(allyloxycarbonyl)glycine, prepared as described by F. Guibe, O. Dangles, and G. Balavione in Tetrahedron Letters, 1986, 27, 2365-2368, 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)glycine 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-9af572c6f13f4f37a3874e6b7e208b6d
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

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