Derivatives of (5-Oxooxazolidin-4-yl)acetic acids in aspartic acid α-carboxyl protection: a word of caution

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Abstract

Isomeric products could be isolated in a reaction of pentafluorophenyl ester of (S)-2-(3-((benzyloxy)-carbonyl)-5-oxooxazolidin-4-yl)acetic acid with aminoacid esters. One product is an expected dipeptide, the isomeric one is an N-hydroxymethylamino succinimide – a product of methylene bridge cleavavge. Steric bulkness of aminoacid esters favors the formation of a peptide, however the reaction selectivity is quite unpredicatable. Moreover, the precise structure assignement requires high-temperature NMR experiments.

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About the authors

V. N. Azev

Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS

Author for correspondence.
Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

A. N. Chulin

Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

M. V. Molchanov

Istitute for Theoretical and Experimental Biophysics RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, Institutskaya ul. 3, Puschino, 142290

A. I. Miroshnikov

Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

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2. Scheme 1. Formation of a mixture of isomeric products in a two-stage synthesis of compound (IV).

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3. Fig. 1. Comparison of two regions of the spectra of the reaction product of compounds (I) and (II): (a) – at 298 K in normal DMSO-d6; (b) – at 298 K in dried DMSO-d6; (c) – at 353 K; (d) – at 383 K. The signal of residual water is marked with an asterisk.

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4. Fig. 2. Comparison of the 6.2–2.6 ppm regions of the 1H NMR spectrum of products containing oxazolidine rings: (a) – compound (I) at 298 K; (b) – compound (I) at 353 K; (c) – starting acid for the synthesis of compound (I) at 353 K; (d) – product (IX) at 353 K; (d) – product (X) at 298 K.

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