Hydrochloric Acid → HCID 15408617, compound

HRID 1607857Notes

Reaction equation

HRID 1607857 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH:2]=[CH2:3].Cl.[C:17](=O)(O)[O-].[Na+]>CO>[CH3:17][O:14][C:13](=[O:15])[C@H:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13968683N-[(2-Propen-1-yloxy)carbonyl]-L-leucine

Product 1

HCID 15408617HCID 15408617, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.06 mol of N-(allyloxycarbonyl)leucine, 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)leucine 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-8c11a2dee50c4df6a369150560292089
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

Loading…