Methanol → O-Acetyl-L-homoserine

HRID 980285Notes

Reaction equation

HRID 980285 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C[OH:6].[NH2:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10]C(O)=O>N1C=CC=CC=1>[CH3:2][C:1]([O:3][CH2:10][CH2:9][C@H:8]([NH2:7])[C:14]([OH:16])=[O:15])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 33032L-Glutamic Acid

Product 1

HCID 439389O-Acetyl-L-homoserine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  1. customto stand at room temperature
  2. stirringwith intermittent shaking for 24 hours
  3. customto form
  4. customthe precipitate was collected on sintered glass
  5. washwashed with two 600 ml portions of ethanol
  6. customThe precipitate was dried in vacuo at room temperature for 3 hours
  7. waitin a vacuum desiccator over Drierite® for 5 hours
  8. customwas further triturated with ether
  9. customdried again

Sources & evidence

ORD record
ord-df3bffbeb1404f54ab7c876f69925b15
Source dataset
uspto-grants-1987_01
Patent number
US04636526

Reaction notes

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