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9-fluorenylmethyl chloroformate preparation method

A technology of fluorenylmethyl chloroformate and methanol, which is applied in the field of preparation of 9-fluorenylmethyl chloroformate, can solve the problem of incomplete reaction, difficult crystallization of products, and high purity of 9-fluorenylmethyl chloroformate No advanced problems, to achieve the effect of mild conditions and simple process

Inactive Publication Date: 2013-11-27
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to propose a method for synthesizing 9-fluorenylmethyl chloroformate, to solve the incomplete reaction of the present method for synthesizing 9-fluorenylmethyl chloroformate, the product is difficult to crystallize, and the purity of 9-fluorene Technical problem of low methyl chloroformate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 9-fluorenemethanol 19.6, chloroform 100ml, and triphosgene 46g into a three-neck flask, turn on the magnetic stirring for 30 minutes, under the ice bath, control the temperature at -5~5℃, dissolve 35ml of diisopropylethylamine in 100 ~150ml of chloroform was added dropwise into the reaction flask, stirred for 1 hour, then heated to 40~60°C, reacted for 2~4 hours, filtered off the white solid, concentrated and recovered chloroform to obtain oily 9-fluorenylmethyl chloroformate, Cryogenically obtained white crystals, 100ml of diethyl ether was washed twice, and dried to obtain 23g of 9-fluorenylmethyl chloroformate with a purity greater than 98%, a melting point of 60-64°C, and a yield of 90%.

Embodiment 2

[0023] Take 9-fluorenemethanol 19.6, carbon tetrachloride 100ml, and triphosgene 46g into a three-neck flask, turn on the magnetic stirring for 30 minutes, under an ice bath, control the temperature at -5 ~ 5°C, add 35ml of diisopropylethylamine Dissolved in 100-150ml of carbon tetrachloride and added dropwise to the reaction flask, stirred for 1 hour, then heated to 50-70°C, reacted for 3-5 hours, filtered off the white solid, concentrated and recovered carbon tetrachloride to obtain oily 9 -Fluorenylmethyl chloroformate, deep cooling to obtain white crystals, 100ml of diethyl ether was divided into two washes, dried to obtain 22.5g of 9-fluorenylmethyl chloroformate with a purity greater than 98%, and a melting point of 61-64°C. The rate is 88%.

Embodiment 3

[0025] Take 19.6 g of 9-fluorenemethanol, 100 ml of chloroform, and 46 g of triphosgene into a three-necked flask, turn on the magnetic stirring for 30 minutes, under an ice bath, control the temperature at -5 to 5°C, and dissolve 18.5 g of 4-dimethylaminopyridine in 100 to Add 150ml of chloroform dropwise into the reaction flask, stir for 1 hour, then heat up to 40-60°C, react for 2-4 hours, filter off the white solid, concentrate and recover chloroform to obtain oily 9-fluorenylmethyl chloroformate, deep Cool to obtain white crystals, wash 100ml of diethyl ether twice, and dry to obtain 24g of 9-fluorenylmethyl chloroformate with a purity of more than 98%, a melting point of 60-64°C, and a yield of 93%.

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Abstract

The present invention relates to a 9-fluorenylmethyl chloroformate preparation method, particularly to an improved method for preparing 9-fluorenylmethyl chloroformate from 9-fluorenylmethanol. The method comprises the following steps: 1) adding chloroform, 9-fluorenylmethanol and triphosgene to a reactor, and stirring for 30 min, wherein raw materials comprise 9-fluorenylmethanol, triphosgene, chloroform and 4-dimethylaminopyridine, and a ratio of the 9-fluorenylmethanol to the triphosgene to the chloroform to the 4-dimethylaminopyridine is 20 g:46 g:200 ml:18.5 g; 2) in an ice bath, adding a chloroform solution of 4-dimethylaminopyridine in a dropwise manner, and carrying out a reaction for 2-4 h; and 3) filtering the reactant in the reactor to obtain a white solid and the filtrate, and sequentially carrying out pressure reduction solvent removing, cryogenic crystallization, organic solvent washing and drying on the filtrate to obtain the white solid 9-fluorenylmethyl chloroformate. The preparation method has characteristics of mild reaction conditions, low cost, simple process, and easy industrialization.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 9-fluorenylmethyl chloroformate. Background technique [0002] 9-fluorenylmethyl chloroformate (Fmoc-Cl) is a white or off-white powder with a melting point of 60-63°C. As an amino-protecting reagent, it is widely used in the field of peptide synthesis. Its stability and alkalinity in acidic conditions The ease of detachment under certain conditions plays a great auxiliary role in promoting the development of the biological field and the research and development of new drugs; as 9-fluorenylmethyl azidoformate (Fmoc-N 3 ) and 9-fluorenylmethylsuccinimide carbonate (Fmoc-OSu) and other synthetic raw materials for amino-protecting agents, and their demand continues to increase. [0003] In recent years, many domestic scholars and experts have made great contributions to the preparation of 9-fluorenylmethyl chloroformate, as stated in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/96C07C68/00
Inventor 彭学东张梅赵金召庞珍强
Owner ZHANG JIA GANG VINSCE BIO PHARM
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