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

HRID 1283881Notes

Reaction equation

HRID 1283881 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>CO>[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 887MethanolSolvent

Procedure

A solution of ethyl DL-phenylglycinate (6.26 g., 35 mmole) and (+)-tartaric acid (5.56 g., 1.05 equiv.) in dry methanol containing benzaldehyde (7% v/v benzaldehyde, 1 equiv; total volume 46 ml.) at 50° was cooled from 50° to 22° and stirred for 25 hours. The solid was filtered off and washed with methanol containing 7% benzaldehyde (15 ml.) then methanol (10 ml.) and dried at 22°/2 mm. for 3 hours to give ethyl D-phenylglycinate (+)-hemitartrate as a mono-methanol solvate (5.50 g., 43%), m.p. 131°-135° [α]D24 - 48° (c 2.68, H2O).

Workup

  1. temperaturewas cooled from 50° to 22°
  2. filtrationThe solid was filtered off
  3. washwashed with methanol containing 7% benzaldehyde (15 ml.)
  4. dry with materialmethanol (10 ml.) and dried at 22°/2 mm

Sources & evidence

ORD record
ord-ec733bcde1af40f89e299dde05a975ab
Source dataset
uspto-grants-1976_08
Patent number
US03976680

Reaction notes

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