تفاعل #342792

ord-22565767e7864b22bae1a3d98cefdd36

معادلة التفاعل

CC(=O)Cl
acetyl chloride
CO
methanol
N[C@@H](CCC(=O)O)C(=O)O
L-glutamic acid
CC(=O)OCC[C@H](N)C(=O)O
γ-methyl L-glutamate

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىto stand at room temperature
  2. 2
    workup.STIRRINGwith intermittent shaking for 24 hours
  3. 3
    أخرىto form
  4. 4
    أخرىthe precipitate was collected on sintered glass
  5. 5
    غسيلwashed with two 600 ml portions of ethanol
  6. 6
    أخرىThe precipitate was dried in vacuo at room temperature for 3 hours
  7. 7
    workup.WAITin a vacuum desiccator over Drierite® for 5 hours
  8. 8
    أخرىwas further triturated with ether
  9. 9
    أخرىdried again

الإجراء التجريبي

A cold solution of 300 ml of acetyl chloride was slowly added to a flask containing 3 liters of methanol. To this mixture was added 442 g of L-glutamic acid. The flask was stoppered and shaken for several minutes to effect solution. The flask was then allowed to stand at room temperature with intermittent shaking for 24 hours. 300 ml of pyridine was added causing a precipitate to form. Upon standing for an additional 48 hours, the precipitate was collected on sintered glass and washed with two 600 ml portions of ethanol and a 250 ml portion of ether. The precipitate was dried in vacuo at room temperature for 3 hours and then in a vacuum desiccator over Drierite® for 5 hours. Pyridine vapors were still perceptible from the precipitate which was further triturated with ether and dried again yielding 201.5 g of the desired γ-methyl L-glutamate as white, shiny plates, m.p. 168°-169° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04698375uspto-grants-1987_10