Chemistry of Natural Compounds

, Volume 15, Issue 3, pp 328–332 | Cite as

Analogs of D(+)-pantothenic acid. V. Synthesis and investigation of the structure of N-pantoyl derivatives of proline

  • T. D. Marieva
  • V. M. Kopelevich
  • V. V. Mishchenko
  • A. K. Starostina
  • L. Yu. Yuzefovich
  • Zh. K. Torosyan
  • V. I. Gunar
Article

Abstract

The synthesis of pantothenic acid analogs is described. Boiling the Na salt of L-proline (L-I) with D-(−)-pantolactone (D-II) in MeONa Yielded 53.91% of N-D-pantoyl-L-proline (III), [α] D 2 ° −52° (c 2; MeOH), and 19.18% of cyclo(N-D-pantoyl-L-proline) (IV), mp 119–121°C (ethanol), [α] D 2 ° −68.9° (c 2; MeOH). The following were obtained similarly: N-L-pantoyl-L-proline, cyclo(N-L-pantoyl-L-proline), N-D-pantoyl-D-proline, cyclo(N-D-pantoyl-D-proline), N-L-pantoyl-D-proline, cyclo(N-D-pantoyl-hydroxyproline), and N-γ-hydroxybutyryl-L-proline. By fusing D-II and DL-I at 140°C cyclo(N-D-pantoyl-DL-proline) and prolylproline anhydride (V) were obtained. Compound (V) with mp 136–138°C was synthesized from DL-1 by heating at 140°C. The PMR spectra of compounds (III-V) are given. The IR spectra of compounds (III and IV) are discussed.

Keywords

Organic Chemistry Proline MeOH Anhydride Pantothenic Acid 

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • T. D. Marieva
  • V. M. Kopelevich
  • V. V. Mishchenko
  • A. K. Starostina
  • L. Yu. Yuzefovich
  • Zh. K. Torosyan
  • V. I. Gunar

There are no affiliations available

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