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Acid-catalyzed rearrangements of 4-carboxy-5-(2′-hydroxyphenyl) prolines

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

Acid hydrolysis of 4-(methoxycarbonyl)-5-(2′-hydroxyphenyl) proline ether ester is accompanied by structural changes of the original compound; when the phenol and methoxycarbonyl groups are trans the proline ring migrates from the ortho to the para position of the phenol ring; when cis the 5-C-N bond is cleaved to form 3-(coumaryl) alanine.

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Literature cited

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    Yu. N. Belokon', N. G. Faleev, V. M. Belikov, V. A. Maksakov & P. V. Petrovskii

Authors
  1. Yu. N. Belokon'
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  2. N. G. Faleev
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  3. V. M. Belikov
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  4. V. A. Maksakov
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  5. P. V. Petrovskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2536–2539, November, 1977.

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Belokon', Y.N., Faleev, N.G., Belikov, V.M. et al. Acid-catalyzed rearrangements of 4-carboxy-5-(2′-hydroxyphenyl) prolines. Russ Chem Bull 26, 2350–2353 (1977). https://doi.org/10.1007/BF00958724

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  • DOI: https://doi.org/10.1007/BF00958724

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