Method for producing peptide compound, reagent for forming protecting group, and condensed polycyclic aromatic hydrocarbon compound
A technology for polycyclic aromatic hydrocarbons and peptide compounds, which is applied in the fields of peptide preparation methods, organic compound preparation, cyanide reaction preparation, etc.
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Embodiment 1
[0613]
[0614] [Chemical formula number 54]
[0615]
[0616] Compound (1-2) (306mg, 0.30mmol), N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine (Fmoc-Leu-OH, 159mg, 0.45 mmol), tetrahydrofuran (1.5 mL), and 4-dimethylaminopyridine (DMAP, 7.0 mg, 0.06 mmol) and diisopropylcarbodiimide (69.7 μL, 0.45 mmol) were added. After stirring the reaction solution for 1 hour, the precipitated solid by adding methanol (15 mL) was filtered and dried under reduced pressure to obtain N-protected C-protected amino acid (1-1) (380 mg, 95.5%).
[0617] In addition, Fmoc represents a 9-fluorenylmethoxycarbonyl group, and Leu represents a leucine residue.
Embodiment 2 and comparative example 1
[0619] In the same manner as the method for obtaining N-protected C-protected amino acid (1-1), compound (1-1), comparative compound (1-1) and N-[(9H-fluoren-9-ylmethoxy) Carbonyl]-L-leucine was fused to synthesize the corresponding N-protected C-protected amino acid.
[0620] 〔Evaluation 1〕
[0621]
[0622] The obtained N-protected C-protected amino acid (10 mg) and 2,6-di-tert-butyl-4-cresol (internal standard: 8 mg) were dissolved in tetrahydrofuran solution (20 mL) and acetic acid (2 mL), respectively, After 3 days at room temperature, the amount of remaining N-protected C-protected amino acid was determined and evaluated according to the following criteria. The results are shown in Table 1.
[0623] About the evaluation of solution stability, the case of "B" or more was set as the pass. The results are shown in Table 1.
[0624] In addition, the higher the solution stability, the higher the stability of the peptide, so it can be said that side reactions can be supp...
Embodiment 3
[0647]
[0648] [Chemical formula number 55]
[0649]
[0650] At room temperature, compound (2-2) (500mg, 0.39mmol), N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine (419mg, 1.18mmol), dichloro Methane (4 mL) was mixed, and diisopropylethylamine (iPr 2 EtN, 207 μL, 1.18 mmol). After heating the reaction solution under reflux and stirring for 20 hours, the solid precipitated by adding acetonitrile (20 mL) was filtered and dried under reduced pressure to obtain N-protected C-protected amino acid (2-2) (550 mg, 82.3 %).
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