Short Note
Version 1
Preserved in Portico This version is not peer-reviewed
(S)-1-Methyl-2-Oxoimidazolidine-4-Carboxylic Acid
Version 1
: Received: 25 May 2024 / Approved: 27 May 2024 / Online: 27 May 2024 (22:20:11 CEST)
A peer-reviewed article of this Preprint also exists.
Dey, A.L.; Motevalli, M.; Abrahams, I.; Wyatt, P.B. (S)-1-Methyl-2-oxoimidazolidine-4-carboxylic Acid. Molbank 2024, 2024, M1835. Dey, A.L.; Motevalli, M.; Abrahams, I.; Wyatt, P.B. (S)-1-Methyl-2-oxoimidazolidine-4-carboxylic Acid. Molbank 2024, 2024, M1835.
Abstract
(S)-1-Methyl-2-oxoimidazolidine-4-carboxylic acid 1 is an analog of (S)-pyroglutamic acid, a key component of naturally occurring peptide hormones and synthetic pharmaceutical candidates. Reaction of (S)-2-amino-3-(methylamino)propionic acid with COCl2 and aqueous NaHCO3 followed by ion exchange afforded 1, which was recrystallized from acetonitrile and then characterized by IR, 1H NMR, 13C NMR, polarimetry, elemental microanalysis, high resolution mass spectrometry and single crystal X-ray diffraction. The acid 1 crystallized in the orthorhombic chiral space group P212121 with cell constants a = 6.2275(4) Å, b = 8.3963(5) Å, c = 24.9490(14) Å. The X-ray crystal structure reveals that two distinct conformers of 1 occur at alternating positions within helices which are supported by hydrogen-bonding. Each molecule of 1 is linked to its two neighbors in the helix by a total of three hydrogen bonds and four molecules of 1 are contained within each turn of the helix. The pattern of hydrogen bonds illustrates a preference for the carboxylic acid group to act as a hydrogen bond donor and for the urea unit to be a hydrogen bond acceptor.
Keywords
X-ray structure; imidazolidine-2-one; amino acid; urea; phosgene
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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