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Synthesis of (1 R )‐(1‐acetamido‐2‐phenylethyl)boronic acid‐1‐ 13 C
Author(s) -
Matteson Donald S.,
Michnick T. John
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580310802
Subject(s) - chemistry , boronic acid , stereochemistry , combinatorial chemistry , medicinal chemistry
(1 R )‐(1‐Acetamido‐2‐phenylethyl)boronic acid‐1‐ 13 C, which is the boron analogue of N ‐acetylphenylalanine, has been synthesized via a modification of the route previously established for the unlabelled compound. The 13 C label is derived from dichloromethane‐ 13 C. The previous conditions utilized excess dichloromethane, but it has now been found that a stoichiometric amount of dichloromethane suffices for the preparation of (dichloromethyl)lithium and its reaction with a boronic ester. Thus, the method has broad potential for the synthesis of compounds bearing 13 C lebels at chiral sites. The 1 H and 13 C NMR spectra of the target compound and the intermediates leading to it are discussed.