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Method for preparing Fmoc-Thr(tBu)-OH

A z-thr, benign solvent technology, applied in the field of preparation of Fmoc-Thr-OH, can solve the problem of high risk, achieve the effects of production safety, improve production efficiency, and improve reaction speed

Inactive Publication Date: 2018-09-28
成都市科隆化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a method for preparing Fmoc-Thr(tBu)-OH for the problem of high risk in the existing Fmoc-Thr(tBu)-OH hydrogenolysis preparation process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A preparation method for Fmoc-Thr(tBu)-OH, comprising the following steps:

[0032] (1) Dissolution: Add Z-Thr(tBu) OMe and its benign solvent to the reactor, mix and stir to dissolve;

[0033] (2) Hydrogenolysis: Add hydrogen donor, pure water and catalyst in sequence to the mixed solution to generate hydrogenolysis reaction;

[0034] (3) Filtration: filter the solution after hydrogenolysis to remove the precipitate;

[0035] (4) Concentration: Concentrate the filtrate obtained in step (3) to remove the benign solvent;

[0036] (5) Saponification: add acetone and pure water to the concentrate obtained in step (4), adjust the pH to 11~12 with an alkaline solution, and saponify to obtain Thr(tBu)-OH;

[0037] (6) Synthesis: Mix Thr(tBu)-OH obtained in step (5) with Fmoc-OSu at a weight ratio of 2:5, and heat to react to obtain Fmoc-Thr(tBu)-OH;

[0038] (7) Dry the Fmoc-Thr(tBu)-OH obtained in step (6).

Embodiment 2

[0040] A preparation method for Fmoc-Thr(tBu)-OH, comprising the following steps:

[0041] (1) Dissolution: add Z-Thr(tBu) OMe and methanol solvent to the reaction kettle, and mix according to the volume ratio of 2.5:3 to obtain the first solution;

[0042] (2) Hydrogenolysis: Add 30 parts of hydrogen donor 1,4-cyclohexadiene, 0.1 part of catalyst and 20 parts of pure water to each part of Z-Thr(tBu)•OMe in parts by weight , a hydrogenolysis reaction occurs. The catalyst comprises 3 parts of platinum, 5 parts of palladium, 20 parts of palladium hydroxide, 7 parts of palladium-polyethyleneimine and 10 parts of nano-alumina in parts by weight.

[0043] (3) Filtration: the precipitate in the solution after hydrogenolysis is taken out by suction filtration to obtain the second solution;

[0044] (4) Concentration: Concentrate the second solution with a rotary evaporator until crystals are precipitated, and remove the methanol solvent. The rotational speed of the rotary evaporato...

Embodiment 3

[0049] A preparation method for Fmoc-Thr(tBu)-OH, comprising the following steps:

[0050] (1) Dissolution: add Z-Thr(tBu) OMe and n-hexane solvent to the reaction kettle, and mix according to the volume ratio of 3:4.5 to obtain the first solution;

[0051] (2) Hydrogenolysis: Add 35 parts of hydrogen donor 1,3-cyclopentanediene, 0.3 parts of catalyst and 20 parts of pure water to each part of Z-Thr(tBu)•OMe in parts by weight. , a hydrogenolysis reaction occurs. The catalyst comprises 4 parts of platinum, 7 parts of palladium, 25 parts of palladium hydroxide, 11 parts of palladium-polyethyleneimine and 15 parts of nano-alumina in parts by weight.

[0052] (3) Filtration: take out the precipitate in the solution after hydrogenolysis by centrifugation to obtain the second solution; the centrifugation speed is 3750r / min, and the centrifugation time is 10min;

[0053](4) Concentration: Concentrate the second solution with a rotary evaporator until crystals are precipitated, and...

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Abstract

The invention discloses a method for preparing Fmoc-Thr(tBu)-OH, and relates to the field of biochemical engineering. The method comprises the following steps of (1) dissolving, wherein Z-Thr(tBu)-OMeis dissolved; (2) hydrogenolysis, wherein a hydrogen donor, pure water and a catalyst are added to be hydrogenated; (3) filtration, wherein the hydrogenated solution is filtered, and precipitation isremoved; (4) concentration, wherein a benign solvent is removed; (5) saponification, wherein acetone and the pure water are added, the pH value is adjusted to be 11-12 by using an alkaline solution,saponification is carried out to obtain Thr(tBu)-OH; (6) synthesis, wherein the Thr(tBu)-OH and Fmoc-OSu react to generate the Fmoc-Thr(tBu)-OH; and (7) drying. The method for preparing the Fmoc-Thr(tBu)-OH has the advantages that the catalyst is adopted to perform catalytic hydrogenation reaction, it is achieved that Z-Thr(tBu)-OH reacts with 1,3-cyclopentane diene at the normal temperature and pressure, the dehydrogenation of carboxybenzyl is achieved, not only is the production safer, but also the reaction speed is effectively improved, and then the production efficiency is improved.

Description

technical field [0001] The invention relates to the field of biochemical industry, in particular to a preparation method of Fmoc-Thr(tBu)-OH. Background technique [0002] A common alkoxycarbonyl amino-protecting group of Fmoc (fluorenylmethyloxycarbonyl). The Fmoc protecting group is extremely stable to acids and is relatively easy to deprotect by a simple amine (not hydrolysis). The protected amine is released as a free base. out. During the preparation of Fmoc-Thr(tBu)-OH, Thr(tBu)-OH was obtained by hydrogenolysis of Z-Thr(tBu)-OH (benzyloxycarbonyl-Thr(tBu)-OH). [0003] In the prior art, the hydrogenolysis reaction of Z-Thr(tBu)-OH needs to first replace the air in the reactor with nitrogen, and then introduce hydrogen. At the same time, the hydrogenation reaction is carried out under the pressure of 0.15~0.2Mpa. After the reaction is completed, the hydrogen in the reactor will also be replaced with nitrogen. Since hydrogen is a flammable and explosive gas, and the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07G99/00
CPCC07G99/00
Inventor 张松张仁友傅建唐波张晓斌吴晓玲张仕君刘林左祥群赵绍益张碧元刘贵明姚国峰何盛东植丽军罗培强管秀君刘勇吴国勇吴秀英
Owner 成都市科隆化学品有限公司
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