1-Benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2- phenylpropan-1-ones:  Mosher-Bt Reagents

Abstract

Benzotriazole derivatives of 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid react with water-soluble amino acids and peptides in an acetonitrile/water (2:1) mixture to give the corresponding amides in quantitative yield.

Recent Advances in Multinuclear NMR Spectroscopy for Chiral Recognition of Organic Compounds

“…An alternative approach to assign the absolute configuration of amino acids using the Mosher’s acid was developed by Katritzky et al [ 40 ]. N -acylbenzotriazoles are stable and crystalline derivatives of carboxylic acids and have advantages mainly when compared to acid chlorides that are unstable, moisture sensitive, difficult to prepare, and need to be stored in a deep freeze.…”

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…Several benzotriazole sulfur reagents 130 have been prepared and used for thioacylations, thiocarbamoylations, alkyl/ alkoxythioacylations, and aryl/alkylthioacylations [186]. Benzotriazole of 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (131) reacted with water-soluble amino acids and peptides in an acetonitrile/water (2 : 1) mixture to give the corresponding Mosher derivative in quantitative yield [187]. Anionic in situ generation of formaldehyde from benzotriazolylmethanol 132 has proved to be a very useful and versatile tool in synthesis [188].…”

One-pot preparation of carbamoyl benzotriazoles and their applications in the preparation of ureas, hydrazinecarboxamides and carbamic esters

“…18 The Katritzky group also demonstrated that no racemization of the amino acid derivative occurred under the same conditions. 19 Bis-nucleophilic hydrazines were also reacted with carbamoyl benzotriazoles (Scheme 4 and Table IV). For methylhydrazine, the more electrophilic nitrogen atom (with methyl attached) was aminoacylated without any promoter and compounds 6a and 6b were obtained in excellent yields (Table IV, entries 1 and 2).…”