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Combined in situ monitoring method for analysis and optimization of the lithiation-fluoroacetylation of N-(4-chlorophenyl)-pivalamide / Tamas A. Godany in Industrial & engineering chemistry research, Vol. 50 N° 10 (Mai 2011) 

Public ISBD [article]  in Industrial & engineering chemistry research > Vol. 50 N° 10 (Mai 2011) . - pp. 5982-5991 Titre : Combined in situ monitoring method for analysis and optimization of the lithiation-fluoroacetylation of N-(4-chlorophenyl)-pivalamide Type de document : texte imprimé Auteurs : Tamas A. Godany, Auteur ; Yorck-Michael Neuhold, Auteur ; Konrad Hungerbuhler, Auteur Année de publication : 2011 Article en page(s) : pp. 5982-5991 Note générale : Chimie industrielle Langues : Anglais (eng) Mots-clés : Optimization  Surveillance  In  situ Résumé : Lithiation-fluoroacetylation of N-(4-chlorophenyl)-pivalamide (NCP) is a key step in the synthesis of a potent inhibitor of the HIV type 1 reverse transcriptase. The reaction comprises a heterogeneous lithiation step catalyzed by the solvent, fluoroacetylation with ethyl-trifluoroacetate (TFAEt), and hydrolysis. We investigate the reaction in our in-house developed small-scale low-temperature reaction calorimeter (CRC.v6 LT) employing in situ monitoring methods, such as reaction calorimetry, in situ spectroscopy (ATR FT-IR and UV/vis), and endoscopy, complemented by off-line GC/FID and GC/MS. The dynamic behavior of the reaction steps including end point prediction/detection is discussed, giving insights into a possible reaction mechanism and optimized reaction conditions. DEWEY : 660 ISSN : 0888-5885 En ligne : http://cat.inist.fr/?aModele=afficheN&cpsidt=24158895 [article] Combined in situ monitoring method for analysis and optimization of the lithiation-fluoroacetylation of N-(4-chlorophenyl)-pivalamide [texte imprimé] / Tamas A. Godany, Auteur ; Yorck-Michael Neuhold, Auteur ; Konrad Hungerbuhler, Auteur . - 2011 . - pp. 5982-5991. Chimie industrielle Langues : Anglais (eng) in Industrial & engineering chemistry research > Vol. 50 N° 10 (Mai 2011) . - pp. 5982-5991 Mots-clés : Optimization  Surveillance  In  situ Résumé : Lithiation-fluoroacetylation of N-(4-chlorophenyl)-pivalamide (NCP) is a key step in the synthesis of a potent inhibitor of the HIV type 1 reverse transcriptase. The reaction comprises a heterogeneous lithiation step catalyzed by the solvent, fluoroacetylation with ethyl-trifluoroacetate (TFAEt), and hydrolysis. We investigate the reaction in our in-house developed small-scale low-temperature reaction calorimeter (CRC.v6 LT) employing in situ monitoring methods, such as reaction calorimetry, in situ spectroscopy (ATR FT-IR and UV/vis), and endoscopy, complemented by off-line GC/FID and GC/MS. The dynamic behavior of the reaction steps including end point prediction/detection is discussed, giving insights into a possible reaction mechanism and optimized reaction conditions. DEWEY : 660 ISSN : 0888-5885 En ligne : http://cat.inist.fr/?aModele=afficheN&cpsidt=24158895