N,N-diethanolaminomethyl polystyrene: An efficient solid support to immobilize boronic acids

Angewandte Chemie - International Edition

Volumn 38, Issue 20, 1999, Pages 3064-3067

  Hall, Dennis G ^a   Tailor, Jyoti ^a   Gravel, Michel ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Boronic acid; Immobilization; Solid phase synthesis

Indexed keywords

BORONIC ACID DERIVATIVE; ETHANOLAMINE DERIVATIVE; N,N DIETHANOLAMINOMETHYLPOLYSTYRENE; POLYSTYRENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; IMMOBILIZATION; MOLECULAR STABILITY; SYNTHESIS;

EID: 0033581550     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3064::AID-ANIE3064>3.0.CO;2-T     Document Type: Article

References (18)

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9. The resulting resin gave a negative outcome with Kaiser's ninhydrin assay, [9] which indicated the absence of any primary and secondary amines originating from incomplete alkylation. The presence of a basic tertiary amine site, however, was shown through a positive reaction with bromophenol blue. The absence of over-alkylation to give a triethanolalkylammonium hydroxide resin was indirectly confirmed by exhaustive acylation with FmocGlyOH (1-hydroxy-1H-benzotriazole, diisopropylcarbodiimide, 4-dimethylaminopyridine; DMF, RT, 6h) followed by UV spectroscopic quantitation of the resulting fulvene - piperidine adduct (Fmoc = fluoren-9-ylmethoxycarbonyl). The loading level obtained therein was in agreement with the formation of two ethanolamine arms per aminomethyl site according to the initial loading of commercial AM-PS. However, a slightly high O/N ratio from combustion analysis of the resin (theoretical = 2.3, experimental = 2.6) may indicate the presence of residual water, or of a few hydroxyethoxyethyl arms formed by ethylene oxide solvolysis. These inhomogeneities do not seem to affect the resin's efficiency.
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11. Purchased from Advanced Chemtech, Inc.
12. Another control experiment ruled out the possibility that a tertiary amine site alone (through formation of a tight acid-base complex) could be sufficient. Diisopropylaminomethyl polystyrene (Argonaut Technologies) failed to couple with 2a under the usual conditions.
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18. Nonoptimized yields of crude isolated compounds of satisfying purity, all characterized by NMR spectroscopy and mass spectrometry.