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Acidolysis

  • Miklos Bodanszky
  • Agnes Bodanszky
Part of the Springer Lab Manual book series (SLM)

Abstract

An about 33% solution of HBr in acetic acid [3] (10 ml) is placed in a 250 ml round bottom flask and benzyloxycarbonyl-glycyl-l-phenylalanine benzyl ester [2] (4.46 g, 10 mmol) is added with swirling. The flask is closed with a cotton-filled drying tube and swirled to effect complete dissolution of the protected dipeptide. Vigorous evolution of CO2 takes place [4] and some evolution of heat can be observed [5]. When the gas evolution ceases (about 20 minutes) [6] dry ether (200 ml) is added with swirling and the reaction mixture is stored in a refrigerator [7] for several hours. The precipitate is collected on a filter, washed with ether (50 ml) and dried over NaOH pellets in vacuo. Glycyl-l-phenylalanine benzyl ester hydrobromide (3.4 g, 87%) can be purified by recrystallization from ethanol-ether and it melts then at 193 °C; correct analytical values are obtained for N and Br.

Keywords

Trifluoroacetic Acid Hydrogen Fluoride Hydrobromic Acid Benzyl Ester Benzyl Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer-Verlag Berlin Heidelberg 1994

Authors and Affiliations

  • Miklos Bodanszky
    • 1
  • Agnes Bodanszky
    • 2
  1. 1.PrincetonUSA
  2. 2.ClevelandUSA

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