Year: 2024
Type: article
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.
Source: Molbank
DOI: 10.3390/m1888
Authors: Majid Motevalli, Isaac Abrahams, Peter Blakskjær, Caroline E. Wyatt, Peter B. Wyatt
Institution: Queen Mary University of London
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $568
OpenAlex ID: W4402860336