2,3-Dihydroxybutanedioic Acid → (R)-Amino-phenyl-acetic acid ethyl ester

HRID 1283884Notes

Reaction equation

HRID 1283884 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].C(O)(=O)C(C(C(O)=O)O)O>CO.CC(C)=O>[CH3:1][CH2:2][O:3][C:4]([C@H:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 409886ethyl 2-amino-2-phenylacetate

Product 1

HCID 6922658(R)-Amino-phenyl-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

A solution of ethyl DL-phenylglycinate (5.051 g., contains 0.05 mole methylene chloride i.e. 27.5 mmole) and (+)-tartaric acid (4.264 g., 28.4 mmole, 1.03 equiv.) in methanol: acetone (1:1, 50 ml.) was stirred at 20° to 25°; crystallisation began immediately. After 231/2 hours the mixture was filtered and the product washed with solvent (2 × 12 ml.) and dried at 24°/2 mm. for 31/2 hours giving ethyl D-phenylglycinate (+)-hemitartrate solvated with 1.0 mole methanol (7.265g., 73%), [α]D24 - 47.4° (c 2.519, H2O).

Workup

  1. customcrystallisation
  2. filtrationAfter 231/2 hours the mixture was filtered
  3. washthe product washed with solvent (2 × 12 ml.)
  4. customdried at 24°/2 mm

Sources & evidence

ORD record
ord-2aa7de642cac42f1a3df62286b682685
Source dataset
uspto-grants-1976_08
Patent number
US03976680

Reaction notes

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