Process for synthesizing carbonochloridic acid 9-fluorene methyl ester

A technology of chloroformic acid and a synthetic method, which is applied in the preparation of phosgene or haloformate, organic chemistry, etc., can solve the problems of high price and toxicity, and achieves the effects of mild conditions, simple process and high yield

Inactive Publication Date: 2008-08-20
BAOSHAN IRON & STEEL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Pyridine has a special odor, is poisonous, and is more expensive

Method used

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  • Process for synthesizing carbonochloridic acid 9-fluorene methyl ester
  • Process for synthesizing carbonochloridic acid 9-fluorene methyl ester
  • Process for synthesizing carbonochloridic acid 9-fluorene methyl ester

Examples

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Embodiment 1

[0026] Embodiment 1: in 250ml there-necked flask, add 7.0 gram solid phosgene, 10 gram purity is the mixed solution (mass ratio is 5: 95) of 99% 9-fluorenemethanol and 100ml toluene and normal hexane, stir in-5 ℃ , add 1.7 g of diethylamine, react for 2 hours, then heat up to 25-30°C, stir for 2 hours, filter to remove solids. The obtained filtrate was cooled in an ice bath for 3 hours, after Fmoc-Cl was fully crystallized and separated out, filtered and dried to obtain 10.52 grams of 9-fluorenylmethyl chloroformate product with a purity of 98.12% (the chromatogram is shown in figure 1 ), yield 79.21%.

Embodiment 2

[0027] Embodiment 2: in 250ml there-necked flask, add 7.0 gram solid phosgene, 10 gram purity be the mixed solution (mass ratio is 5: 95, gas chromatography detection, prepared), stirred at -5°C, added 1.7 g of diethylamine, reacted for 2 hours, raised the temperature to 25-30°C, stirred for 2 hours, and filtered to remove solids. The obtained filtrate was cooled in an ice bath for 3 hours, after Fmoc-Cl was fully crystallized and separated out, filtered and dried to obtain 10.40 grams of 9-fluorenylmethyl chloroformate product with a purity of 98.05% (the chromatogram is shown in figure 2 ), yield 78.25%.

Embodiment 3

[0028] Embodiment 3: in 250ml there-necked flask, add 8.0 gram solid phosgene, 10 gram purity is the mixed solution (mass ratio is 5: 95) of 9-99% 9-fluorenemethanol and 100ml toluene and normal hexane, at-5 ℃ Stir, add 2.5 g of diethylamine, react for 2 hours, heat up to 25-30°C, stir for 2 hours, filter to remove solids. The obtained filtrate was cooled in an ice bath for 3 hours, after Fmoc-Cl was fully crystallized and separated out, filtered and dried to obtain 10.77 grams of 9-fluorenylmethyl chloroformate product with a purity of 98.47% (the chromatogram is shown in image 3 ), yield 81.40%.

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Abstract

The invention provides a method for synthesizing chlorinated formic acid 9-fluoren methyl, which comprises the following steps: (1) 9-fluoren methyl and triphosgene are reacted for 0.5 to 3 hours in ice bath, under the existence of catalyst and in organic solvent; the catalyst is chosen from N with nucleophilicity, N-dimethylformamide, acetone, diisopropyl ethyl amine, diethylamine, triethylamine, ethyleendiamine, putrescine, imidazole, and the solvent is chosen from benzene, toluene, cyclohexane, hexane, heptane, cyclopentane, dichloromethane, chloroform and the compound thereof; (2) the temperature raises to 20 to 50 DEG C, and the mixture reacts for 1 to 5 hours. The method for synthesizing chlorinated formic acid 9-fluoren methyl adopts safe solid phosgene as reactant, and is simple in technique, convenient in safety, mild in condition, high in yield and easy in realization of industrialization production; the solvent can be used repeatedly after being processed simply, and the products do not need to be refined, and purity is up to more than 98 percent.

Description

technical field [0001] The invention relates to a synthesis method of aromatic esters, in particular to a synthesis method of 9-fluorenylmethyl chloroformate. Background technique [0002] 9-Fluorenylmethyl chloroformate (Fmoc-Cl for short) is a white needle-like crystal with a melting point of 61.5-63°C and a structural formula of: [0003] [0004] Fmoc-Cl can be directly used as an amino-protecting agent for peptide synthesis. The fundamental difference from Boc-protecting agents is that the alkali-removable Fmoc is used as the protecting group for the α-amino group. In the synthesis of some amino groups containing unstable amino groups under acidic conditions Residue polypeptide, has special advantages; Fmoc-Cl can also be used as a synthetic 3 ) and intermediates of amino-protecting agents such as 9-fluorenylmethylsuccinimide carbonate (Fmoc-OSu). [0005] According to the literature published at home and abroad, Fmoc-Cl is synthesized by reacting 9-fluorenemethano...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C68/02C07C69/96
Inventor 张秀云陈叶飞夏烨
Owner BAOSHAN IRON & STEEL CO LTD
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