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Method for synthesizing 9-fluorenylmethoxycarbonyloxy succinimide ester

Inactive Publication Date: 2010-09-01
BAOWU CHARCOAL MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The object of the present invention is to propose a kind of method for synthesizing 9-fluorenylmethoxycarbonyl succinimide ester, to solve the method productive rate of synthesizing 9-fluorenylmethoxycarbonyl succinimide ester now is low, reaction time Long, the technical problem that the purity of the reaction product is difficult to reach more than 98%

Method used

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  • Method for synthesizing 9-fluorenylmethoxycarbonyloxy succinimide ester
  • Method for synthesizing 9-fluorenylmethoxycarbonyloxy succinimide ester
  • Method for synthesizing 9-fluorenylmethoxycarbonyloxy succinimide ester

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Experimental program
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Embodiment 1

[0034] Add a solution of 7.0 g (0.0603mol) N-hydroxysuccinimide, 10 g (0.0387mol) Fmoc-Cl with a purity of 99%, and 100ml (66.5g) n-hexane into a 250ml three-necked flask, and place it in an ice bath Stir, add 1.7 g (0.0232 mol) of diethylamine. After reacting for 2 hours, the temperature is raised to 25-30° C., stirred for 2 hours, filtered to obtain a solid, and dried to obtain 10.52 g of Fmoc-ONSu product with a purity of 98.12%. The rate is 79.08%. (Purity is chemical purity, the same below.)

Embodiment 2

[0036] Add 6 grams (0.0517mol) of N-hydroxysuccinimide, 10 grams (0.0387mol) of Fmoc-Cl with a purity of 99%, and 100ml (68.0g) of n-heptane into a 250ml three-necked flask, and place it in an ice bath. Add 1.7 g (0.0232mol) of diethylamine with medium stirring. After reacting for 2 hours, the temperature is raised to 25-30°C, stirred for 2 hours, filtered to obtain a solid, and dried to obtain 10.40 g of Fmoc-ONSu product with a purity of 98.31%. The yield was 78.32%.

Embodiment 3

[0038] Add 5.6 grams (0.0603mol) of N-hydroxysuccinimide, 10 grams (0.0387mol) of Fmoc-Cl with a purity of 99% and 100ml (66.5g) of recovered n-hexane into a 250ml three-necked flask, and place it in an ice bath Stir, add 1.7 g (0.0232 mol) of diethylamine. After 2 hours of reaction, heat to 25-30°C, stir for 2 hours, filter to obtain solids, and dry to obtain 10.61 g of Fmoc-ONSu product with a purity of 98.05%. The yield is 79.89%.

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Abstract

The invention relates to a method for synthesizing an amino acid protective agent, in particular to a method for synthesizing 9-fluorenylmethoxycarbonyloxy succinimide ester (abbreviated as Fmoc-ONSu), which comprises the following steps of: a), adding an organic solvent, Fmoc-Cl, N-hydroxysuccimide and a catalyst into a reactor to perform a reaction, wherein the Fmoc-Cl and the N-hydroxysuccimide are reactants, and the solvent is a non-protonic solvent; and b) filtering the reaction product in the reactor to obtain solid and residual liquid, and drying the solid to obtain the 9-fluorenylmethoxycarbonyloxy succinimide ester product. The method has the advantages of simple process, safety, convenience, mild condition and high yield. The synthesized Fmoc-ONSu product has a purity of over 98percent and therefore does not need to be refined.

Description

Technical field [0001] The invention relates to a method for synthesizing an amino acid protective agent, in particular to a method for synthesizing 9-fluorene methoxycarbonyl succinimide ester (abbreviated as Fmoc-ONSu). Background technique [0002] Fmoc-ONSu is a white needle-like crystal with a melting point of 148~150℃ and its structural formula is: [0003] [0004] As one of the most important amino acid protective agents for peptide synthesis, Fmoc-ONSu has a very broad market prospect. In the prior art, the synthetic route of Fmoc-ONSu uses Fmoc-Cl (fluorene methoxycarbonyl chloride) and N-hydroxysuccinimide to react in one step in an organic solvent to obtain the product. The overall reaction equation is as follows: [0005] [0006] As described by Paul BW et al. in the literature Int. J. Peptide Protein Res. 27, 1986, 398-400, the synthesis method of Fmoc-ONSu generally adopts Fmoc-Cl and N-hydroxysuccinimide in dioxygen In the six-ring solvent, the reaction is carried...

Claims

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Application Information

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IPC IPC(8): C07D207/404
Inventor 陈叶飞夏烨
Owner BAOWU CHARCOAL MATERIAL TECH CO LTD