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

HRID 1283882Notes

Reaction equation

HRID 1283882 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.CC(C)=O>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 180AcetoneHCID 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

A solution of ethyl DL-phenylglycinate (5.00 g., 28 mmole) and (+)-tartaric acid (4.18 g., 28 mmole, 1 equiv.) in ethanol (50 ml.) was made at 58°. The solution was cooled, acetone (4.1 ml., 55.6 mmole, 2 equiv.) was added and the mixture was stirred at 20° to 25° for 165 hours. The solid was filtered off, washed with ethanol (2 × 10 ml.) and dried at 26°/2 mm. for 41/2 hours to give ethyl D-phenylglycinate (+)-hemitartrate as a monoethanol solvate (9.338 g., 89%), [α]D -46.5° (c 2.5 H2O).

Workup

  1. customwas made at 58°
  2. temperatureThe solution was cooled
  3. filtrationThe solid was filtered off
  4. washwashed with ethanol (2 × 10 ml.)
  5. customdried at 26°/2 mm

Sources & evidence

ORD record
ord-81da3982a726476eadb90ec3b57d2021
Source dataset
uspto-grants-1976_08
Patent number
US03976680

Reaction notes

Loading…