Version 1
: Received: 7 September 2024 / Approved: 8 September 2024 / Online: 9 September 2024 (08:28:10 CEST)
How to cite:
Motevalli, M.; Abrahams, I.; Blakskjær, P.; Wyatt, C. E.; Wyatt, P. B. (R)-2-Amino-1-Hydroxyethylphosphonic Acid. Preprints2024, 2024090592. https://doi.org/10.20944/preprints202409.0592.v1
Motevalli, M.; Abrahams, I.; Blakskjær, P.; Wyatt, C. E.; Wyatt, P. B. (R)-2-Amino-1-Hydroxyethylphosphonic Acid. Preprints 2024, 2024090592. https://doi.org/10.20944/preprints202409.0592.v1
Motevalli, M.; Abrahams, I.; Blakskjær, P.; Wyatt, C. E.; Wyatt, P. B. (R)-2-Amino-1-Hydroxyethylphosphonic Acid. Preprints2024, 2024090592. https://doi.org/10.20944/preprints202409.0592.v1
APA Style
Motevalli, M., Abrahams, I., Blakskjær, P., Wyatt, C. E., & Wyatt, P. B. (2024). (R)-2-Amino-1-Hydroxyethylphosphonic Acid. Preprints. https://doi.org/10.20944/preprints202409.0592.v1
Chicago/Turabian Style
Motevalli, M., Caroline E. Wyatt and Peter B. Wyatt. 2024 "(R)-2-Amino-1-Hydroxyethylphosphonic Acid" Preprints. https://doi.org/10.20944/preprints202409.0592.v1
Abstract
(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis and anion exchange chromatography. Recrystallization from water-ethanol gave 2, which was characterized by IR, 1H NMR, 13C NMR, 31P NMR, polarimetry, elemental microanalysis, high-resolution mass spectrometry and single-crystal X-ray diffraction. The acid 2 crystallized in the orthorhombic chiral space group P212121 with cell constants a = 6.303(2) Å, b = 7.104(2) Å, c = 11.627(3) Å. The X-ray crystal structure confirmed the (R)-configuration of 2 and revealed that 2 is zwitterionic in the solid state, with extensive intermolecular hydrogen bonding between the hydroxyl, ammonium cation and phosphonate anion groups.
Chemistry and Materials Science, Organic Chemistry
Copyright:
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