Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, A new synthetic method of this compound is introduced below., Formula: C10H6F3NO2
General procedure: To synthesize Boc-Gly-AFC, 1 eq of Boc-Gly-OH and 1 eq of AFC2 were dissolved in anhydrous pyridine and cooled in a ice/NaCl bath to 15 C. To this mixture 1.4 eq of POCl3 was added dropwise in 10 min. The reaction was carried out at -15 C and the progress was monitored using TLC analysis. After the reaction was complete (60 min) the mixture was dissolved in ethyl acetate and extracted with 5% citric acid (2x), 5% NaHCO3 (2x),and brine (2x). The organic fraction was dried over MgSO4 and ethyl acetate was then removed under reduced pressure to obtain Boc-Gly-AFC, which was used for further synthesis without additional purification. In a separate synthesis N-acetylated tripeptides with the free carboxylic group at the C terminus were synthesized similarly as described previously and used without further purification (41). To synthesize Ac-peptide-Gly-AFC substrates, 1 eq of Boc-Gly-AFC was dissolved in 50% TFA in dichloromethane (with 2.5% of triisopropylsilane as a scavenger) and the Boc deprotection reaction was carried out for 30 min. After the reaction was completed, TFA and dichloromethane were removed under reduced pressure to obtain NH2-Gly-AFC. Next, NH2-Gly-AFC was dissolved solved in a minimal amount of N,N-dimethylformamide, followed by the addition of 1 eq of Ac-peptide-COOH and 1 eqof HBTU (O-benzotriazole-N,N,N’,N’-tetramethyluronium hexafluorophosphate). Finally, 3 eq of DIPEA (N,N-diisopropylethylamine) were added and the coupling reaction was carried out for 3 h. After the reaction was completed, as judged by HPLC analysis, the mixture was diluted in ethyl acetate and extracted with 5% citric acid (2x), 5% NaHCO3 (2x), and brine (2x). The organic fraction was dried over MgSO4 and the ethyl acetate was then removed under reduced pressure to obtain crude Ac-peptide-Gly-AFC. Next, all protecting groups were removed in 50% TFA in dichloromethane (with 2.5% of triisopropylsilane as a scavenger) for 1 h. Finally, the crude productwas purified by HPLC on a Waters M600 solvent delivery module with a Waters M2489 detector system using a semi-preparative Waters Spherisorb S10ODS2 column. The solvent composition was as follows: phase A (water, 0.1% TFA) and phase B (acetonitrile, 0.1% TFA). The purity of each compound was verified by an analytical HPLC system using a Waters Spherisorb S5ODS2 column. The molecular weight of each Ac-peptide-Gly-AFC substrate was determined by high-resolutionmass spectrometry using a High Resolution Mass Spectrometer WATERS LCT premier XE with Electrospray Ionization (ESI) and Time of Flight (TOF) module.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Rajkovi?, Jelena; Poreba, Marcin; Cagli?, Dejan; Vidmar, Robert; Wilk, Aleksandra; Borowik, Agata; Salvesen, Guy; Turk, Vito; Drag, Marcin; Turk, Boris; Journal of Biological Chemistry; vol. 290; 47; (2015); p. 28231 – 28244;,
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