Ammonia → HCID 12192619, compound

HRID 2392826Notes

Reaction equation

HRID 2392826 reaction equation
Cl.COC(=O)[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[CH3:15][Mg]I.[Cl-].[NH4+].N.C([O:23][CH2:24][CH3:25])C>O>[NH2:6][C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:24]([CH3:25])([OH:23])[CH3:15]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 178418373HCID 178418373, compound

Product 1

HCID 12192619HCID 12192619, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-Phenylalanine methyl ester hydrochloride (7) (8 g, 37.09 mmol) was added in portions, during 15 minutes, to a solution of methylmagnesium iodide [prepared from methyl iodide (13.76 ml, 222.6 mmol)] in diethyl ether (304 ml) and refluxed for 6 hours. To promote hydrolysis, a saturated solution of ammonium chloride (19.38 g, 370.9 mmol) in water (70 ml) was added dropwise with vigorous stirring. The insoluble product was filtered off through celite, and the organic layer was separated and dried with sodium sulphate. Concentration in vacuo gave a colourless oil. The aqueous layer was made alkaline by addition of aqueous ammonia. The product was extracted with diethyl ether, dried with sodium sulphate and concentrated in vacuo. The oily residues were then combined and distilled giving the title compound (8) (2.686 g, 41%).

Workup

  1. temperaturerefluxed for 6 hours
  2. customhydrolysis
  3. filtrationThe insoluble product was filtered off through celite
  4. customthe organic layer was separated
  5. dry with materialdried with sodium sulphate
  6. concentrationConcentration in vacuo
  7. customgave a colourless oil
  8. extractionThe product was extracted with diethyl ether
  9. dry with materialdried with sodium sulphate
  10. concentrationconcentrated in vacuo
  11. distillationdistilled

Sources & evidence

ORD record
ord-a58812a0a2cd4e4a88247cd76b1dbe80
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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