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Method for preparing cyclodipeptide cyclo(L-Asp-L-Pro)

A technology of aspartame and cyclic dipeptide, applied in the direction of organic chemistry, etc., can solve the problem of no synthesis method of aspartame cyclic dipeptide, achieve considerable economic and practical value, simple reaction operation, and easy post-processing effect

Inactive Publication Date: 2008-03-19
HYBIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is no report on the synthesis method of aspartame dipeptide

Method used

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  • Method for preparing cyclodipeptide cyclo(L-Asp-L-Pro)
  • Method for preparing cyclodipeptide cyclo(L-Asp-L-Pro)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1, L-L type aspartame dipeptide

[0032] 1. Add L-Pro-OMe (450mg, 3.4mmol), Boc-L-Asp(OBzl)-OH (904mg, 2.8mmol), DCC (803mg, 3.9mmol) into a 100ml round bottom flask, mix all , add DCM (15ml), stir at room temperature for 20min, TLC traces the completion of the reaction, evaporate the solvent on the rotary evaporator, dissolve with ethyl acetate (15ml), filter, spin dry to obtain a yellow gum, and then use ethyl acetate The ester (15ml) was dissolved, and there was a small amount of insoluble matter, filtered, and finally washed with 0.1N HCl, saturated NaHCO 3 Wash with saturated NaCl for 2-3 times to obtain 1.20 g of oil, yield: 99%. Electrospray mass spectrometry (ESI-MS) and nuclear magnetic resonance (1HNMR 13 C NMR) measurement, proves that the obtained product is correct.

[0033] 2. Add 200 mg (0.46 mmol) of N-tert-butoxycarbonyl-β-benzyl aspartame in a 50 ml round-bottomed flask, add 10 mg of Pd / C, and take out the air in the three-necked flask. ...

Embodiment 2

[0036] Embodiment 2, L-L type aspartame dipeptide

[0037] 1. Add L-Pro-OMe (450mg, 3.4mmol), Boc-L-Asp(OBzl)-OH (904mg, 2.8mmol), DCC (803mg, 3.9mmol) into a 100ml round bottom flask, mix all , add DCM (15ml), stir at room temperature for 20min, TLC traces the completion of the reaction, evaporate the solvent on the rotary evaporator, dissolve with ethyl acetate (15ml), filter, spin dry to obtain a yellow gum, and then use ethyl acetate The ester (15ml) was dissolved, and there was a small amount of insoluble matter, filtered, and finally washed with 0.1N HCl, saturated NaHCO 3 Wash with saturated NaCl for 2-3 times to obtain 1.20 g of oil, yield: 99%. electrospray mass spectrometry (ESI-MS) and nuclear magnetic resonance ( 1 HNMR 13 C NMR) measurement, proves that the obtained product is correct.

[0038] 2. Add 200 mg (0.46 mmol) of N-tert-butoxycarbonyl-β-benzyl aspartame in a 50 ml round-bottomed flask, add 2 ml of saturated HCI ether solution, then add 3 ml of ether,...

Embodiment 3

[0041] Embodiment 3, D-L type aspartame dipeptide

[0042] 1. Add L-Pro-OMe (450mg, 3.4mmol), Boc-D-Asp(OBzl)-OH (904mg, 2.8mmol), DCC (803mg, 3.9mmol) into a 100ml round bottom flask, and mix them all , add DCM (15ml), stir at room temperature for 20min, TLC traces the completion of the reaction, evaporate the solvent on the rotary evaporator, dissolve with ethyl acetate (15ml), filter, spin dry to obtain a yellow gum, and then use ethyl acetate The ester (15ml) was dissolved, and there was a small amount of insoluble matter, filtered, and finally washed with 0.1N HCl, saturated NaHCO 3 Wash with saturated NaCl for 2-3 times to obtain 1.19 g of oil, yield: 98%. Electrospray mass spectrometry (ESI-MS) and nuclear magnetic resonance (1HNMR 13 C NMR) measurement, proves that the obtained product is correct.

[0043] 2. Add 200 mg (0.46 mmol) of N-tert-butoxycarbonyl-β-benzyl aspartame in a 50 ml round-bottomed flask, add 2 ml of saturated HCl in ether, then add 3 ml of ether,...

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Abstract

The invention relates to a preparation method of cyclic dipeptide, in particular to a preparation method of aspartic ammonia prolinase cyclic dipeptide. The technical scheme of the invention includes four steps; firstly, starting from proline methyl ester and N-tertbutyloxycarbonyl-Beta-benzyl aspartic acid, the protective aspartic ammonia prolinase cyclic dipeptide methyl ester is obtained; secondly, under the acidic condition, the protective aspartic ammonia prolinase cyclic dipeptide methyl ester is deprotected; thirdly, cyclization occurs under the alkaline condition; fourthly, the aspartic ammonia prolinase cyclic dipeptide is finally generated by catalytic hydrogenolysis. The invention skillfully utilizes a gas phase method to synthesize the aspartic ammonia prolinase cyclic dipeptide, the technique is characterized in simple reaction and operation, easy-processing, little environmental pollution, low cost, etc., and the invention can be widely applied to the field of the design and synthesis of drugs.

Description

technical field [0001] The invention relates to a method for preparing cyclic dipeptide, in particular to a method for preparing aspartame cyclic dipeptide. Background technique [0002] Cyclic dipeptides are often found in natural products. Such compounds are found in humans, vertebrates, invertebrates, plants, fungi, and bacteria. Many cyclic dipeptides have strong physiological activities, such as inhibiting lactation Animal cell growth cycle, uptake of dopamine by nerve endings, secretion of prolactin and feeding of white mice, etc. Some cyclic dipeptides are widely present in the human central nervous system and gastrointestinal tract, and have their stereoselective receptors in the liver and adrenal glands. External application causes many physiological activities, such as affecting the reproduction of mice, inhibiting the release of insulin and glucagon, etc. Thus, cyclic dipeptides are platforms for some drug designs. [0003] At present, there is no report on the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/38
Inventor 马亚平钟飞
Owner HYBIO PHARMA
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