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Preparation method of (S)-2-((9H-fluoren-9-methoxycarbonyl)methylamino)-5-amino-5-oxovaleric acid

A kind of oxopentanoic acid preparation method, methoxycarbonyl technology, applied in (S)-2-((9H-fluorene-9-methoxycarbonyl)methylamino)-5-amino-5-oxo In the field of valeric acid production method, it can solve the problems of high raw material cost and three wastes, and achieve the effect of cheap reaction raw materials

Inactive Publication Date: 2021-01-05
上海吉奉生物科技有限公司
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Problems solved by technology

It mainly solves the technical problems of high cost of raw materials and production of more three wastes in existing synthesis methods

Method used

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  • Preparation method of (S)-2-((9H-fluoren-9-methoxycarbonyl)methylamino)-5-amino-5-oxovaleric acid

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Embodiment Construction

[0013] step 1:

[0014] Add L-glutamic acid (10.0 g, 68.0 mmol), water (100 mL) and acetone (100 mL) into a 500 mL reaction flask, and add sodium bicarbonate (14.3 g, 170.0 mmol) and 9-Fluorenylmethyl-N-succinimidyl carbonate (25.2 g, 74.8 mmol), stirred at room temperature overnight, the reaction solution was diluted with water (100 mL), extracted with ethyl acetate (3 x 100 mL) and separated , the aqueous phase was adjusted to pH=2-3 with 6 M hydrochloric acid, and a large amount of white solid was precipitated; after filtration, it was dried at 50°C to obtain a white solid, compound 1 (23.1 g, 62.6 mmol, 92%). LC-MS (ESI): m / z 368.15 [M-H] - .

[0015] Step 2:

[0016] Add compound 1 (30.0 g, 81.2 mmol), paraformaldehyde (5.0 g, 166.7 mmol) and p-toluenesulfonic acid (2.0 g, 11.6 mmol) into a 150 mL reaction flask, raise the temperature to 130 ° C, and heat to reflux for 3 hours until no more water flows out of the trap. Cool to room temperature, wash the reaction solu...

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Abstract

The invention relates to a preparation method of (S)-2-((9H-fluoren-9-methoxycarbonyl)methylamino)-5-amino-5-oxo-valeric acid. The invention mainly solves the technical problems of high raw material cost and more generated three wastes in the existing synthesis method. The method comprises the following steps: in a sodium bicarbonate solution, reacting Lglutamic acid with 9-fluorenylmethyl-N-succinimido carbonate at room temperature to generate a compound 1, in methylbenzene subjected to heating reflux, carrying out a dehydration condensation reaction process on the compound 1 and paraformaldehyde under the catalytic action of p-toluenesulfonic acid to generate a compound 2, in an ethyl acetate solution, carrying out acylation reaction on the compound 2, ammonium carbonate, pyridine and di-tert-butyl dicarbonate at room temperature to generate a compound 3, and reacting the compound 3 with triethylsilane and trifluoroacetic acid in a dichloromethane solution at room temperature to generate a target compound 4. The product provided by the invention is used for synthesizing Callipeltin series natural products with effective cytotoxicity and anti-HIV activity, and is also an importantintermediate for synthesizing various peptide active substances.

Description

technical field [0001] The present invention relates to a synthesis method of (S)-2-((9H-fluorene-9-methoxycarbonyl)methylamino)-5-amino-5-oxopentanoic acid (CAS: 910056-51-8) . Background technique [0002] In recent years, the biological activity of Callipeltin series natural products has been deeply studied. It has been reported that, as cyclic depsipeptides, callipeltin A and B not only have anti-HIV and anti-fungal activities, but also have cytotoxicity to several cancer cells in human body. In 2002, D'Auria's team successfully isolated CallipeltinE, an acyclic hexapeptide, from the marine sponge Latrunculia sp. In 2006, Purdue University chemists obtained two isomers 1 and 5 of Callipeltin E by solid-phase synthesis using Fmoc-amino acids as intermediates. [0003] [0004] As an amino acid derivative, (S)-2-((9H-fluorene-9-methoxycarbonyl)methylamino)-5-amino-5-oxopentanoic acid is an important intermediate for the synthesis of Callipelten series natural product...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C269/06C07C271/22C07D263/26
CPCC07C269/04C07C269/06C07D263/26C07C2603/18
Inventor 徐红岩马敬祥
Owner 上海吉奉生物科技有限公司
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