Liquid-phase synthesis method of semaglutide side chain
A liquid-phase synthesis and side-chain technology, which is applied in the field of liquid-phase synthesis of semaglutide side-chains, can solve the problem of not finding a pure liquid-phase synthesis method for the side-chain, and achieves easy control of the reaction process, simple production process, and easy process. workable effect
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[0057] Example 1
[0058] according to figure 1 The synthetic route shown is the liquid phase synthesis of semaglutide side chain:
[0059] a. Preparation process of compound 3
[0060] Dissolve 1.05g of compound 2 (10mmol) in 50ml of DCM solution and place it in a nitrogen-protected flask. After the above mixed solution has dropped to 0°C, carefully add (Boc) to the above solution 2 O (2.62 g, 12 mmol). The mixture was stirred for 12 hours, then the crude material was concentrated in vacuo. Purified by flash column chromatography to obtain a colorless oil with a yield of 95%.
[0061] b. Preparation process of compound 4:
[0062] Add 3.08g (9.5mmol) of compound 3, 8.6g (4eq) benzyl bromoacetate and 2.75g (2.1eq) potassium carbonate into a round bottom flask. The reaction temperature was raised to 50℃. After 18 hours of reaction, the plate was observed. Relatively complete; washing with water, EA extraction 2-3 times, washing with saturated brine, anhydrous Na 2 SO 4 Dry, P:E=6:1 an...
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[0080] Example 2
[0081] a. Preparation process of compound 3
[0082] Dissolve 5mmol / ml of compound 2 (1ml) in DCM solution and place it in a nitrogen-protected flask. After the above mixture drops to 0℃, add 1eq of Et dropwise 3 N; 20 minutes later, slowly add 2mmol / ml Trt-Cl (2.5ml) mixture dropwise to the above-mentioned mixture solution, remove the ice bath after 10 minutes dropwise addition; stir at room temperature, and observe the plate after 1h, the reaction is complete . Wash with water, extract with DCM 2-3 times, wash with saturated brine, anhydrous Na 2 SO 4 After drying, P:E=5:1 through the column, collecting the product, the yield is 85%.
[0083] b. Preparation process of compound 4:
[0084] Add 694mg (2mmol) of compound 3, 1832mg (4eq) of benzyl bromoacetate and 580mg (2.1eq) of potassium carbonate into a round-bottomed flask. The reaction temperature was raised to 50°C. After 18 hours of reaction, the reaction was observed by spot plate and the reaction was relati...
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