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Active compound and application thereof in protection of side-chain carboxyl compound

A compound and chain carboxyl technology, which is applied in the field of protection of biochemical products and side chain carboxyl compounds, can solve the problem of inability to obtain amino acids with high chiral purity, and achieve the effect of high chiral purity

Active Publication Date: 2022-05-13
上海嘉莱多生物技术有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The literature Levinson, Adam (JACS, 2017, 139 (22), 7632-7639) reported that in dichloromethane solvent, DCC was used as a dehydrating agent, and DMAP was used as a catalyst to obtain 3-methyl-3-pentanol protected asparagus Amino acid, because the strong basic DMAP is used as a catalyst in this method, it will lead to racemization of the obtained protected amino acid product, and it is impossible to obtain amino acid with high chiral purity

Method used

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  • Active compound and application thereof in protection of side-chain carboxyl compound
  • Active compound and application thereof in protection of side-chain carboxyl compound
  • Active compound and application thereof in protection of side-chain carboxyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] A kind of synthetic method of active compound, the step of synthesizing active compound comprises:

[0105] Step 1: In a 10L reaction flask equipped with a thermometer, add N,N-diisopropylcarbodiimide 1.75kg, 3-methyl-3-pentanol 2.8kg, and cuprous chloride 420g;

[0106] Step 2: Stir the reaction at 25°C for 3.5 days;

[0107] Step 3: Suction filtration to obtain 4.5 kg of active compound.

[0108] The structure of the multi-active compound is tested and analyzed by NMR, and the NMR spectrum is as follows figure 1 As shown, the structural formula of the compound can be obtained from the NMR spectrum as:

[0109]

Embodiment 2

[0111] A preparation method of an amino acid protected by a polyalkyl-substituted-3-pentanol group, the preparation steps comprising:

[0112] S1: At 25°C, in a 10L reaction flask equipped with a thermometer, sequentially add 3L tetrahydrofuran, 3L water, 300g sodium bicarbonate, 350g aspartic acid-1-benzyl ester, 580g FmocOSu, and stir for 14h at 25°C. The liquid was adjusted to weakly acidic with an aqueous hydrochloric acid solution with a molar concentration of 3 mol / L, 1 L of ethyl acetate was added to extract the aqueous phase twice, the organic phases were combined, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, concentrated, and washed with acetic acid. Ethyl ester petroleum ether was crystallized to obtain 320g Fmoc-aspartic acid-1-benzyl ester;

[0113] S2: At 25°C, in a 10L reaction flask equipped with a thermometer, add 3.2L tetrahydrofuran, 320g Fmoc-aspartic acid-1-benzyl ester, dropwise add 4.5kg of the active compound in Exampl...

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Abstract

The invention relates to protection of biochemical products and side-chain carboxyl compounds, belongs to the IPC classification number of C07D307 / 82, and particularly relates to protection of active compounds and side-chain carboxyl compounds. The structural formula of the active compound is shown in the specification, and R1, R2 and R3 are independently or jointly hydrogen or an electron donating group. The active compound is used for protecting side chain carboxyl compounds.

Description

technical field [0001] The invention relates to the protection of biochemical products and side chain carboxyl compounds, the IPC classification number is C07D307 / 82, in particular to an active compound and its application in the protection of side chain carboxyl compounds. technical background [0002] In the field of biomedicine, the precursors of some drugs generally contain many active groups. In the preparation of drugs, these active groups need to be protected first to ensure the smooth synthesis of drugs. Peptides have a wide range of uses in the field of biomedicine. Among them, amino acids are the precursors of polypeptides, and derivatives of chiral protected aspartic acid and glutamic acid are important components of many biologically active peptide-containing natural products, and are widely used in the preparation of polypeptide drugs. Protected amino acids are The most basic raw materials for synthetic peptide technology, including 3-methyl-3-pentanol, 2,3,4-tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/70C07C273/18C07C269/04C07C269/06C07C271/22
CPCC07C275/70C07C273/1809C07C269/04C07C269/06C07C2603/18C07B2200/07C07C271/22Y02P20/55
Inventor 袁美斐郑栋赵国栋
Owner 上海嘉莱多生物技术有限责任公司
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