Benzaldehyde → (R)-Amino-phenyl-acetic acid ethyl ester

HRID 1283880Notes

Reaction equation

HRID 1283880 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.C(=O)C1C=CC=CC=1>C(O)C>[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

5

Reactant 3

HCID 240BenzaldehydeHCID 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 702EthanolSolvent

Procedure

Solutions of ethyl DL-phenylglycinate (5.0 g., 27.95 mmole), (+)-tartaric acid (4.417 g., 29.45 mmole, 1.05 equiv.), and benzaldehyde (2.85 ml., 27.95 mmole, 1.0 equiv.) in ethanol (total volume 47 ml.) were mixed at 58°. The solution was cooled to 20° to 26° and stirred for 24 hours to give a white solid which was washed with ethanol (2 × 10 ml.), and dried at 29°/2 mm. for 6 hours to give ethyl D-phenylglycinate (+)-hemitartrate as a mono-ethanol solvate (7.95 g., 76%), [α]D20 -47° (c 2.5, H2O).

Workup

  1. temperatureThe solution was cooled to 20° to 26°
  2. customto give a white solid which
  3. washwas washed with ethanol (2 × 10 ml.)
  4. customdried at 29°/2 mm

Sources & evidence

ORD record
ord-1816b2b9c9ff4b33a1f1d1418de06ab9
Source dataset
uspto-grants-1976_08
Patent number
US03976680

Reaction notes

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