Priprava etravirina, 3-fenilpiridina i 7-etiltriptofola protočnim sustavima

master's thesis

• Title (english): Preparation of etravirine, 3-phenilpyridine, and 7-etyltriptophol using flow reactors
• Author: Franjo Krajinović
• Mentor: Ernest Meštrović (mentor)
• Committee member: Vesna Petrović Peroković (predsjednik povjerenstva)
• Committee member: Ernest Meštrović (član povjerenstva)
• Committee member: Branimir Bertoša (član povjerenstva)
• Committee member: Sanda Rončević (član povjerenstva)
• Committee member: Ivan Kodrin (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2018-09-04, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Istražene su kemijske reakcije priprave poznatih spojeva: etravirina, 3-fenilpiridina i 7-
etiltriptofola u protočnim reaktorima. Priprava etravirina najprije je uspješno provedena u
šaržnom procesu uz kalijev karbonat kao bazu te je izrađen model praćenja reakcijske
kinetike. Priprava etravirina u protočnom reaktoru nije bila uspješna ni nakon promjene baze
(trietilamin i amonijak umjesto kalijeva karbonata). Priprava 3-fenilpiridina u protočnom
reaktoru također je bila neuspješna zbog gubitka katalitičke moći korištenog katalizatora. Spoj
7-etiltriptofol uspješno je pripremljen u protočnom reaktoru te su optimirani reakcijski uvjeti.
Konverzija reaktanta praćena je infracrvenom spektroskopijom i tekućinskom
kromatografijom visoke učinkovitosti uz 7-etiltriptofol i etravirin kao standarde. Standardi su
prethodno identificirani spektroskopijom protonske nuklearne magnetske rezonancije i
tekućinskom kromatografijom spregnutom sa spektrometrijom masa.

Abstract (english)

Known chemical reactions were examined: etravirine, 3-phenylpyridine, and 7-ethyltryptofole
in the flow reactors. Preparation of etravirine was first completed in a batch process with
potassium carbonate as base and model for monitoring reaction kinetic was designed.
Preparation of etravirine in flow reactor failed after the base change (triethylamine and
ammonia). Preparation of 3-phenilpyridine failed due to depletion of the catalitic power of the
catalyst. Compound 7-ethyltriptophol was successfully prepared and reaction conditions were
optimized. The reactants conversion was monitored by means of the infrared spectroscopy
and high-performance liquid chromatography. Compounds 7-ethyltryptofole and etravirine
were used as reference standards. Standards were identified by means of proton nuclear
magnetic resonance and liquid chromatography-tandem mass spectrometry.

• Keywords: dizajn eksperimenata; etravirin; 7-etiltriptofol; 3-fenilpiridin; protočni reaktori
• Keywords (english): design of experiments; flow reactors; 7-ethyltryptofole; etravirine; 3-phenyl pyridine
• Language: croatian
• URN:NBN: urn:nbn:hr:217:462176
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2020-09-25
• Created on: 2018-11-19 11:15:13