Synthesis Of H-Gly-Phene Lab Report

Abstract: This experiment synthesized H-Gly-Phe-OH dipeptide using “Fmoc chemistry”. The first part of experiment was the synthesis of L-phenylalanine methyl ester hydrochloride. The methyl ester can be synthesised by reaction of thionyl chloride, SOCl2 and dry methanol with L-phenylalanine under reflux condition. The peptide bond was formed later in the experiment, where HBTU, DiPEA and a solution of Fmoc-Gly-OH in DMF were added to a solution of L-phenylalanine methyl ester hydrochloride in DMF. The product formed was the protected dipeptide, Fmoc-Gly-Phe-OMe. The deprotection then took place in which ethanolic sodium hydroxide was used as a base to remove the Fmoc group and thus the exposed amine was neutral. The final product was H-Gly-Phe-OH
L-phenylalanine methyl ester hydrochloride, C10H14CINO2 | 0.43 | 215.68 | 0.002 | - | - | DMF | - | 73.09 | - | 0.948 | 5 | Diethyl ether | - | 74.12 | - | 0.7134 | 50 | 1 M HCl | - | 36.46 | - | 1.490 | 50 | Water | - | - | - | - | 3 x 50 | Brine | - | - | - | - | 50 | Fmoc-Gly-Phe-OMe, C27H26N2O5 | 0.46 | 458.52 | 0.001 | - | - | 1 M ethanolic sodium hydroxide | - | - | - | - | 5 | Acetic acid | 0.52 | 60.05 | 0.009 | 1.049 | 0.5 | Table of hazard assessment : Thionyl chloride, SOCl2 | * Reacts violently with water * Harmful by inhalation and if swallowed * Contacts with water liberates toxic gas * Causes severe burns * corrosive | * rinse immediately with plenty of water if contact with eyes * wear suitable protective clothing * wear gloves
Methanol | * highly flammable * toxic by inhalation, in contact with skin and if swallowed * vapour may cause drownziness and dizziness | * keep container tightly closed * keep away from source of ignition * do not empty into drains | Acetic acid | * flammable * corrosive * causes severe burns | * do not breathe gas, vapour, fumes, spray * rinse immediately in case contact with eyes | N,N-diisopropylethylamine, DiPEA | * highly flammable * harmful * dangerous for environment * corrosive, causes burns | * keep away from source of ignition * do not enter drains * wear gloves and suitable protective clothing | Dimethyl formamide, DMF | * harmful by inhalation and in contact with skin * may cause harm to unborn child * irritating to eyes | * avoid exposure * wear gloves and glasses * do not swallow | Diethyl ether | * extremely flammable * may form explosive peroxide * harmful by inhalation and if swallowed * vapour may cause drowsiness and dizziness | * keep container in well ventilated place * keep away from source of ignition * do not empty into drains | Hydrochloric acid, HCl | * corrosive * toxic | * wear safety glasses and gloves * work in fumehood