DOMINO REACTION IN SYNTHESIS 2-(p-HYDROXYPHENYL)GLYCINE AS PRECURSOR OF ANTIBIOTIC AMOXICILLIN

• Main Author: Setiawan, Haris
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/35162
• Institution: Institut Teknologi Bandung

The compound (R)-(-)-2-(p-hydroxyphenyl)glycine was the side group of antibiotic class beta lactam amoxicillin. Industrially, this compound was obtained from separation of its racemic product via crystallization diastereomer salt of each enantiomer with an chiral compound. Asymmetric synthesis to generate directly the enantiomer 2-(p-hydroxyphenyl)glycine economically would be very benefit because it could avoid separation process racemic mixture which always result low rendement. This compound could be synthesized via domino reaction from mixtures of glyoxylic acid, phenol, and ammonium salt. This research has carried out the modification general procedure of synthesis 2-(p-hydroxyphenyl)glycine via utilizing diammonium tartaric as nitrogen salt in this domino reaction in order to had chiral characteristic in reaction condition. At first procedure, the mixtures of phenol, glyoxylic acid, and ammonium acetate was refluxed for 48 hours at 28-42°C within water solvent. The yield product of ammonium acetate gave specific rotation ?? ?20 = -5,9° (c = 0,013 M, water) with rendemen 3,12%. At second procedure, the mixtures of phenol, glyoxylic acid, and diammonium tartaric was refluxed for 48 hours at 27- 38°C within water solvent. The present of optical rotation showed that tartaric utilization at system reaction could give chiral condition in reaction. The output compound 2-(p-hydroxyphenyl)glycine was characterized physicochemically using NMR, FTIR, MS, and UV.