Sinteza amidov ketopinske kisline

Pavlin, Gašper (author), Grošelj, Uroš (mentor)

Iz (1S)-(+)-10-kafrasulfonske kisline sem prek štirih reakcij uspešno pripravil želeni N-benzilamid ketopinske kisline. Za sintezo ketopinske kisline sem poskusil dva sintezna postopka. Prvi je dal s PCl5 slab izkoristek in nizko čistost nastale spojine, zato sem se odločil za drug postopek z uporabo SOCl2, ki je tudi dal boljše rezultate. N-benzilamid ketopinske kisline pa ni bil prvič pripravljen v okviru mojega eksperimentalnega dela, saj je spojina literaturno znana, bila pa je prvič v celoti okarakterizirana.

• Language: Slovenian
• Keywords: organokataliza, kiralna pomagala, ketopinska kislina.
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-139378
• COBISS.SI-ID: 124529923
• Publication date in RUL: 01.09.2022

Secondary language

• Language: English
• Title: Synthesis of ketopinic acid amides

Abstract

I successfully prepared the desired N-benzylamide of ketopinic acid from (1S)-(+)-10-camphorsulfonic acid in four reaction steps. I tried two procedures for the synthesis of ketopinic acid. The first one with PCl5 gave poor yield and low purity of the resulting compound, so I decided on another procedure with SOCl2, which gave better results. N-benzylamide was not prepared for the first time as part of my experimental work, the compound is known from the literature, but it was fully characterized for the first time.

• Keywords: organocatalysis, chiral auxiliaries, ketopinic acid