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Synthesis method of N-Fmoc-3-aminopropionic acid derivative

A technology for the synthesis of n-fmoc-3-, which is applied in the field of synthesis of N-fmoc-3-aminopropionic acid derivatives, can solve the problems of no reports, etc., and achieve high yield, few steps, and easy-to-obtain raw materials Effect

Inactive Publication Date: 2022-02-01
苏州爱玛特生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Yet as the synthetic method of unnatural amino acid N-Fmoc-3-alanine derivative, there is no any report yet

Method used

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  • Synthesis method of N-Fmoc-3-aminopropionic acid derivative
  • Synthesis method of N-Fmoc-3-aminopropionic acid derivative
  • Synthesis method of N-Fmoc-3-aminopropionic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of N-Fmoc-N-2-methoxyethyl-Beta-alanine

[0051]

[0052]The first step: under ice bath conditions, under the protection of argon, (10.3g, 100.00mmol) methyl allanate, (9.27mL, 101.50mmol) chloroethyl methyl ether, (54.2g, 166.40mmol) Cesium carbonate and (200 mL) ultra-dry DMF were added to a 500 mL round bottom flask respectively, and after stirring for 15 minutes, the mixture was heated to room temperature, and stirred for 5 h. After the reaction was completed, extracted with ethyl acetate, dried the organic layer over anhydrous magnesium sulfate, purified by column chromatography, and eluted with ethyl acetate / petroleum ether (V / V=20 / 1) to obtain 3-((2-methoxyethyl (17.33 g, 93%) of methyl)amino)propionate.

[0053] 1 H NMR (400MHz, CDCl 3 )δ3.63(s,3H),3.55(t,2H),3.36(s,3H),3.13(q,2H),2.97(m,2H),2.50(t,2H).

[0054] The second step: Dissolve (10.95g, 67.95mmol) 3-((2-methoxyethyl)amino) propionate methyl ester in (400mL) (V / V / V=4 / 1 / 1) tetrahydrofura...

Embodiment 2

[0058] Synthesis of N-Fmoc-N-2-Ethoxyethyl-Beta-Alanine

[0059]

[0060] The raw material of this embodiment is methyl allanate (100.00mmol) and 2-ethoxyl chloroethane (101.50mmol), other are the same as embodiment 1, the total yield of three-step reaction: 84.9%.

[0061] 1 H NMR(400MHz,DMSO)δ7.92(dd,2H),7.76(m,2H),7.59(td,2H),7.47(td,2H),4.39(d,2H),4.29(td,1H) ,3.69(td,2H),3.56(m,6H),2.70(t,2H),1.15(t,3H).

Embodiment 3

[0063] Synthesis of N-Fmoc-N-3-methoxypropyl-Beta-alanine

[0064]

[0065] The raw material of this embodiment is methyl allanate (100.00mmol) and 3-chloropropyl methyl ether (101.50mmol), and other are the same as embodiment 1, the total yield of three-step reaction: 84.3%.

[0066] 1 H NMR(400MHz,DMSO)δ7.86(dd,2H),7.72(m,2H),7.56(td,2H),7.44(td,2H),4.47(d,2H),4.28(td,1H) ,3.52(t,2H),3.37(dt,4H),3.19(s,3H),2.66(t,2H),1.88(p,2H).

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Abstract

The invention relates to a synthesis method of an N-Fmoc-3-aminopropionic acid derivative. The method comprises the following steps: (1) reacting a compound (I) with a compound (II) in the presence of a solvent and alkali to obtain a compound (III); (2) carrying out a hydrolysis reaction on the a compound (III) to obtain a compound (IV); and (3) reacting the compound (IV) with fluorenylmethoxycarbonyl succinimide in the presence of the alkali and the solvent to obtain a compound (V) that is the N-Fmoc-3-aminopropionic acid derivative. A process route of the N-Fmoc-3-aminopropionic acid derivative is developed in the invention, makes up the blank of the synthesis method of the substance in the prior art, and the synthesis method is simple, few in steps, high in product yield, easily available in adopted raw materials and low in synthesis cost.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of N-Fmoc-3-aminopropionic acid derivatives. Background technique [0002] In polypeptide drugs, peptide substances have the advantages of high efficiency and small side effects, but they also have the disadvantages of being easily degraded by proteases in the body, not easy to pass through the blood-brain barrier, and having a short half-life. Natural amino acids can enhance their resistance to degradation, or increase their affinity and bioavailability with receptors. It is also possible to introduce unnatural amino acids into proteins or polypeptides, and conduct site-specific modifications to study biological activities. In this way, unnatural amino acids are useful. Unnatural amino acids cannot be obtained from nature and need to be synthesized artificially. [0003] However, there is no report on the synthesis method of the...

Claims

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Application Information

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IPC IPC(8): C07C269/04C07C271/22
CPCC07C269/04C07C227/20C07C227/16C07C271/22C07C229/12
Inventor 汪明中朱明新苏道李金金
Owner 苏州爱玛特生物科技有限公司
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