The preparation method of fmoc-β-ala-gly-oh
A -bt, -su technology, applied in the field of preparation of Fmoc-β-Ala-Gly-OH, can solve the problems of low product purity, low production efficiency, high cost, etc., and achieves cost reduction, low cost, and production steps. short effect
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Embodiment 1
[0054] Add 40.8g of Fmoc-β-Ala-OSu, 100mL of tetrahydrofuran, 200mL of water, 0.2mol of Gly-Na, and 3g of ytterbium boride into the reaction flask, and stir to react. When TLC (thin-layer chromatography) detects that there is no Fmoc-β-Ala-OSu in the reaction system, the reaction is complete. The reaction solution that has completed the above reaction is concentrated in vacuum to a volume of ≤50mL, and 200mL of ethyl acetate and 50mL of water are added, and acidified to pH with hydrochloric acid. ≤2, separate the liquid; wash the ester layer 3 times with 50 mL of saline. Concentrate the ester layer to 80 mL, crystallize, filter, and dry to obtain 35 g of white solid with a yield of 95.1%. The solid was stirred with 100 mL of ethyl acetate at room temperature for 4 hours, filtered, rinsed with 100 mL of ethyl acetate, and dried to obtain 30.6 g of a white solid with a yield of 82.9%. Confirmed by MS and NMR, the white solid is Fmoc-β-Ala-Gly-OH, and the HPLC purity of the prod...
Embodiment 2
[0056] Add 85.6g of Fmoc-β-Ala-OBt, 200mL of dioxane, 400mL of water, 0.4mol of Gly-Na, and 5g of ytterbium boride into the reaction flask, and stir to react. When TLC (thin-layer chromatography) detects that there is no Fmoc-β-Ala-OBt in the reaction system, the reaction is complete, and the reaction solution that has completed the above reaction is concentrated in vacuum to a volume of ≤100ml, and 400mL ethyl acetate and 100mL water are added, and hydrochloric acid is acidified to pH ≤2, separate the liquid; wash the ester layer 3 times with 100 mL of saline. The ester layer was concentrated to 150 mL, crystallized, filtered, and dried to obtain 71 g of a white solid with a yield of 96.4%. The solid was stirred overnight at room temperature with 200 mL of ethyl acetate, filtered, rinsed with 200 mL of ethyl acetate, and dried to obtain 62.6 g of a white solid with a yield of 85.0%. Compared with the sample obtained in Example 1, it was confirmed that the white solid was Fmo...
Embodiment 3
[0058] Add 47.2g of Fmoc-β-Ala-ONB, 100mL of tetrahydrofuran, 200mL of water, 0.15mol of Gly-Na, 4g of ytterbium boride into the reaction flask, and stir the reaction. When TLC (thin-layer chromatography) detects that there is no Fmoc-β-Ala-ONB in the reaction system, the reaction is complete, and the reaction solution that has completed the above reaction is concentrated in vacuum to a volume of ≤ 100ml, added 200mL of water, acidified with hydrochloric acid to pH ≤ 2, and filtered; Rinse 3 times with 100 mL of brine, and collect the solid. 35.3 g of a white solid was obtained with a yield of 95.9%. The solid was stirred with 100 mL of ethyl acetate at room temperature for 8 hours, filtered, rinsed with 50 mL of ethyl acetate, and dried to obtain 30.2 g of a white solid with a yield of 82.0%. Compared with the sample obtained in Example 1, it was confirmed that the white solid was Fmoc-β-Ala-Gly-OH, and the HPLC purity of the product was 99.11%.
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