ISSN:
1573-8388
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00566086
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