Methanol → Methyl 3-amino-3-phenylpropionate

HRID 1881679Notes

Reaction equation

HRID 1881679 reaction equation
S(Cl)(Cl)=O.[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9].[CH3:17]O>>[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([O:10][CH3:17])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 69189DL-beta-Phenylalanine

Product 1

HCID 2755328Methyl 3-amino-3-phenylpropionate

Procedure

Thionyl chloride (19.1 g, 162 mmol) was added dropwise to a solution, cooled to 0° C., of 3-amino-3-phenylpropionic acid (8.9 g, 54 mmol) in methanol (150 ml). The reaction mixture was then heated under reflux for 12 h (TLC control). The solvent was removed completely and the residue was dried in vacuo. The crude product was employed in the next stage without further purification.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 12 h (TLC control)
  3. customThe solvent was removed completely
  4. customthe residue was dried in vacuo
  5. customThe crude product was employed in the next stage without further purification

Sources & evidence

ORD record
ord-93741d92824a4cefa7194e5a0493cdc7
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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