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Synthesis of (1R)-(1-acetamido-2-phenylethyl)boronic acid-1-13C

✍ Scribed by Donald S. Matteson; T. John Michnick

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
364 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

(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.

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