Method for synthesizing N-fluorene methoxycarbonyl-N-trityl-D-glutamine
A technology of fluorene methoxycarbonyl and trityl, which is applied in the synthesis field of N-fluorene methoxycarbonyl-N-trityl-D-glutamine-OH), and can solve the problem of D-glutamine synthesis The problem of high cost, to achieve the effect of reducing production costs
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Embodiment 1
[0036] Example 1, referring to the synthetic route, react glutamic acid and Z-Cl in sodium hydroxide solution at 0-15°C to obtain Z-D-Glu-OH. Z-D-Glu-OH was dissolved in DMF, and triethylamine and benzyl bromide were added to react for 24 hours to obtain Z-D-Glu-OBzl. Dissolve 10mmol Z-D-Glu-OBzl in 100mlTHF, add 10mmolET 3 N, add 10mmol of ClCOOEt at -10~-20°C, add 60mmol of ammonia water after 15-30min, react at room temperature for 6hr, and post-process to obtain product 3 with a yield of 62%. Dissolve 10 mmol of compound 3 and 20 mmol of trityl alcohol in 300 ml of HAc, add 1 mmol of sulfuric acid and 20 mmol of acetic anhydride, react at 60° C. for 8 hours, and post-process to obtain product 4 with a yield of 50%. 10 mmol of compound 4 was dissolved in methanol, 0.3 g of 10% Pd / C was added, and reacted with hydrogen gas for 24 hrs to obtain product 5 with a yield of 92%. Dissolve 10 mmol of compound 5 in saturated sodium bicarbonate and dioxane, add 10 mmol of Fmoc-Osu,...
Embodiment 2
[0037] Example 2, dissolve 10mmol Z-D-Glu-OBzl in 100mlTHF, add 10mmolET 3 N, add 10mmol ClCOOEt at -10~-20°C, add 40mmol ammonia water after 15-30min, react at room temperature for 16hr, and post-process to obtain product 3 with a yield of 60.5%. Dissolve 10 mmol of compound 3 and 20 mmol of trityl alcohol in 300 ml of HAc, add 1 mmol of sulfuric acid and 20 mmol of acetic anhydride, react at 50° C. for 24 hours, and post-process to obtain product 4 with a yield of 48%. 10 mmol of compound 4 was dissolved in methanol, 0.6 g of 5% Pd / C was added, and reacted with hydrogen gas for 36 hrs to obtain product 5 with a yield of 91.5%. All the other are identical with embodiment 1.
Embodiment 3
[0038] Example 3, dissolve 10mmol Z-D-Glu-OBzl in 100ml ethyl acetate, add 10mmolET 3 N, add 10mmol ClCOOEt at -10~-20°C, add 20mmol ammonia water after 15-30min, react at room temperature for 24hr, and post-process to obtain product 3 with a yield of 60%. Dissolve 10 mmol of compound 3 and 20 mmol of trityl alcohol in 300 ml of HAc, add 1 mmol of sulfuric acid and 20 mmol of acetic anhydride, react at 45°C for 24 hrs, and post-process to obtain product 4 with a yield of 47%. 10 mmol of compound 4 was dissolved in methanol, 0.6 g of 10% Pd / C was added, 10 ml of cyclohexene was added and refluxed for 8 hours, and post-treatment was performed to obtain product 5 with a yield of 90%. Dissolve 10 mmol of compound 5 in saturated sodium bicarbonate and dioxane, add 10 mmol of Fmoc-Cl, react for 4 hours, and post-process to obtain product 6. All the other are identical with embodiment 1.
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