Methanol → 4-Amino-L-phenylalanine methyl ester

HRID 36126Notes

Reaction equation

HRID 36126 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>C(OCC)(=O)C>[CH3:18][O:10][C:9](=[O:11])[C@H:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:13][CH:12]=1)[NH2:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1510014-Aminophenylalanine

Product 1

HCID 206108304-Amino-L-phenylalanine methyl esterYield 88.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of p-aminophenylalanine (2.05 g, 9.9 mmol) in methanol (100 ml) at 0° C. was added thionyl chloride (20 ml) dropwise. Upon complete addition the reaction mixture was heated under reflux. After 24 hours the reaction mixture was cooled and reduced under pressure to give a brown oil. The brown oil was taken up in ethyl acetate (200 ml) and washed with saturated sodium bicarbonate solution (200 ml). The aqueous layer was further extracted with ethyl acetate (5×200 ml). The combined organic layer was dried over MgSO4 and reduced under pressure to yield the title compound as a brown solid (1.7 g, 88.5%).

Workup

  1. additionUpon complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux
  4. temperatureAfter 24 hours the reaction mixture was cooled
  5. customto give a brown oil
  6. washwashed with saturated sodium bicarbonate solution (200 ml)
  7. extractionThe aqueous layer was further extracted with ethyl acetate (5×200 ml)
  8. dry with materialThe combined organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-8532da8425fd4449b98d17aac0460488
Source dataset
uspto-grants-1995_05
Patent number
US05412145

Reaction notes

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