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Method for efficient selective preparation of fatty diacid mono-tert-butyl ester

A technology of fatty diacid and mono-tert-butyl ester, which is applied in the field of biomedicine, can solve the problems of selectivity, cost, and unsatisfactory yield, and achieve the effects of wide applicability, good selectivity, and high yield

Active Publication Date: 2019-05-21
富乐马鸿凯(大连)医药有限公司
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AI Technical Summary

Problems solved by technology

[0015] Since known methods cannot meet the demands in industry, especially in the field of biomedicine, in terms of selectivity, cost, and yield, there is still a need for an efficient and selective preparation of mono-tert-butyl fatty acid suitable for industrial scale-up Methods

Method used

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  • Method for efficient selective preparation of fatty diacid mono-tert-butyl ester
  • Method for efficient selective preparation of fatty diacid mono-tert-butyl ester
  • Method for efficient selective preparation of fatty diacid mono-tert-butyl ester

Examples

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preparation example 1

[0068] Preparation Example 1: Synthesis of mono-tert-butyl octadecanedioate

[0069] Step 1: Under nitrogen protection, 1.30 kg of octadecanedioic acid, 130 g of concentrated sulfuric acid and 7.2 L of methanol were heated to reflux for 8 hours, and the reaction progress was detected by HPLC. After the reaction was completed, the reaction temperature was cooled to 0° C. to 5° C., a large amount of solids precipitated, stirred for 2 hours, filtered, and the wet cake was dried to obtain 1.41 kg of dimethyl octadecanedioate, with a yield of 100%. The obtained product was identified by HPLC.

[0070] see figure 1 , the integration results measured by HPLC are shown in Table 1 below.

[0071] Table 1

[0072]

[0073] Step 2: Mix 1.41kg of dimethyl octadecanedioate solid obtained in step 1 with 704g of barium hydroxide octahydrate and 15L of methanol, and then stir the mixed suspension at 20°C to 25°C for 24 hours, The reaction solution was detected by HPLC. After the react...

preparation example 2

[0086] Preparation Example 2: Synthesis of Eicosanedioic Acid Mono-tert-Butyl Ester

[0087] Step 1: Under nitrogen protection, 3.0 kg of eicosanedioic acid, 282 g of concentrated sulfuric acid and 20 L of methanol were heated to reflux for 8 hours, and the reaction progress was detected by HPLC. After the reaction was completed, the reaction temperature was cooled to 0°C to 5°C, a large amount of solids were precipitated, stirred for 2 hours, filtered, and the wet cake was dried to obtain 3.20 kg of dimethyl eicosanedioate with a yield of 98%. The obtained product was identified by HPLC.

[0088] table 5

[0089]

[0090] Step 2: Add 3.20 kg of dimethyl eicosanedioate solid obtained in step 1 to 1.6 kg of barium hydroxide octahydrate and 32 L of methanol, and let the suspension stir at 20°C to 25°C for 24 hours, and detect the reaction by HPLC liquid. After the reaction was completed, the barium salt of the product was filtered out. Mix the barium salt with 30L of wate...

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Abstract

The invention relates to a method for efficient selective preparation of fatty diacid mono-tert-butyl ester. The method comprises the following steps: Step 1, under the action of an acidic catalyst, fatty diacid and alcohol are subjected to an esterification reaction to obtain fatty diester; Step 2, under the alkaline condition, fatty diester obtained in the step 1 is subjected to selective hydrolysis to obtain fatty diacid monoester; Step 3, the fatty diacid monoester obtained in the step 2 undergoes tert-butyl esterification to obtain fatty diacid asymmetric diester; Step 4, under the alkaline condition, the fatty diacid asymmetric diester obtained in the step 3 is subjected to selective hydrolysis to obtain fatty diacid mono-tert-butyl ester, wherein n is an integer of 9-30; and R is C1-C8 linear alkyl group. The method of the invention is simple to operate, and the product purity is high and yield is high. The method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a method for efficiently preparing mono-tert-butyl fatty diacid. Background technique [0002] Long-chain fatty diacids and their derivatives are often used in a series of high-value-added special chemicals such as synthetic drugs, special materials, and spices, and play an important role in prolonging drug efficacy and pharmacokinetics in some known drug molecules. Impact. At present, more and more drugs are developed to try the structure of long-chain fatty carboxylic acid. [0003] For example, in Novo Nordisk (China) Pharmaceutical Co., Ltd.’s insulin degludec, the first ultra-long-acting basal insulin analog approved by the China Food and Drug Administration (CFDA), its molecular structure is characterized by a long-chain fatty diacid It is connected to the lysine residue at position B29 of insulin through a glutamic acid molecule, and the structure is shown in the fol...

Claims

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Application Information

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IPC IPC(8): C07C69/34C07C67/08C07C67/313
Inventor 赵新俊刘凯孙利权刘世旭陈有刚冯言枢高汉荣
Owner 富乐马鸿凯(大连)医药有限公司
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