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Synthesis method of polyketone intermediate

A synthesis method and intermediate technology, applied in the field of synthesis of polyketone intermediates, capable of solving problems such as long synthesis routes and difficult industrial production

Active Publication Date: 2021-11-23
SHANGHAI RUN BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] This method has a long synthetic route, and the total yield of polyketone intermediates is only about 6.6%, which is difficult to be practically used in industrial production

Method used

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  • Synthesis method of polyketone intermediate
  • Synthesis method of polyketone intermediate
  • Synthesis method of polyketone intermediate

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preparation example Construction

[0041] The synthetic method of described polyketone intermediate comprises the following steps:

[0042] (1) in the presence of the first acid binding agent, the compound having the structure shown in formula 1 and N,O-dimethylhydroxylamine hydrochloride are subjected to ring-opening reaction to obtain the compound having the structure shown in formula 2;

[0043]

[0044] (2) the compound with the structure shown in formula 2 is subjected to the first substitution reaction with the methylating reagent to obtain the compound with the structure shown in formula 3:

[0045]

[0046] (3) in the presence of the second acid binding agent, the compound having the structure shown in formula 3 and diphenylphosphoryl azide carry out NHS ester reaction to obtain an intermediate product;

[0047] The intermediate product is subjected to a second substitution reaction with N-acetyl cysteamine to obtain a compound having the structure shown in formula 4;

[0048]

[0049] (4) the...

Embodiment 1

[0092] according to figure 1 The route is synthesized:

[0093] first step

[0094] 1.1 Under nitrogen protection, add 150mL of dry dichloromethane, 13.2g (135.3mmol) of N,O-dimethylhydroxylamine hydrochloride to a 150mL three-necked flask, add 30g (296.5mmol) of triethylamine dropwise, and stir at 20°C Reaction 0.5h.

[0095] 1.2 Control the temperature below 20°C, add 30g (122.8mmol) of 3-tert-butyldimethylsiloxyglutaric anhydride to the above system in batches, and stir at room temperature for 8h after the addition.

[0096] 1.3TLC traced the complete reaction, poured the reaction solution into 150g of ice water, added dilute hydrochloric acid to adjust the pH value to 4, separated the liquid, and extracted the water phase with 200mL dichloromethane for 3 times, washed 2 times with 100mL water, washed with saturated saline, and anhydrous sulfuric acid Dried with magnesium, filtered, concentrated and dried by water pump and oil pump to obtain 34 g of light brown oil, yiel...

Embodiment 2

[0109] according to figure 1 The route to synthesize:

[0110] first step

[0111] 1.1 Add 600 mL of methylene chloride, 50 g (512.6 mmol) of O,N-dimethylhydroxylamine hydrochloride to a 1000 mL three-necked flask with mechanical stirring, dropwise add 112 g (1.1 mol) of triethylamine, and stir the reaction at 15 to 30 °C 1 to 3 hours.

[0112] 1.2 90 g (368.3 mmol) of 3-tert-butyldimethylsilyloxyglutaric anhydride was added in batches at a temperature of 15-20 °C, and the reaction was stirred at room temperature for 12 h.

[0113] 1.3 TLC tracking reaction is complete, pour into 400mL ice water, adjust pH=5 with citric acid aqueous solution, separate liquid and extract the aqueous phase with 600mL dichloromethane 3 times, wash twice with 500mL water, wash with saturated brine, and dry over anhydrous magnesium sulfate, Filtration and concentration gave 100 g (327.3 mmol) of light brown-yellow oil, yield: 88.9%.

[0114] Step 2:

[0115] 2.1 Under nitrogen protection, add ...

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Abstract

The invention provides a synthesis method of a polyketone intermediate, and belongs to the technical field of organic synthesis. The synthesis method provided by the invention comprises the following steps: in the presence of a first acid-binding agent, carrying out ring-opening reaction on a compound with a structure as shown in a formula 1 and N, O-dimethyl hydroxylamine hydrochloride to obtain a compound with a structure as shown in a formula 2; (2) carrying out first substitution reaction on the compound with the structure as shown in the formula 2 and a methylation reagent to obtain a compound with a structure as shown in a formula 3: (3) in the presence of a second acid-binding agent, carrying out NHS ester reaction on the compound with the structure as shown in the formula 3 and diphenyl azide phosphate to obtain an intermediate product; carrying out second substitution reaction on the intermediate product and N-acetyl cysteamine to obtain a compound with a structure as shown in a formula 4; and (4) performing deprotection reaction on the compound with the structure as shown in the formula 4 to obtain the polyketone intermediate with the structure as shown in the formula A. The method is short in synthetic route and high in total yield of products.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing a polyketone intermediate. Background technique [0002] Polyketides are a large class of natural products produced by bacteria, fungi and plants by successive condensation reactions of lower carboxylic acids. compounds that are active against fungi, amphotericin), parasites (such as avermectin, nemadectin), cancer (such as doxorubicin, enediynes), and some antifungal polyketides also have immunosuppressive activity (such as Patoxin, FK506), it is widely used in medicine, animal husbandry and agriculture. [0003] Nowadays, more and more people pay more and more attention to polyketide compounds, which is mainly due to the fact that these compounds have: (1) unparalleled biological activity, and the drugs formed by polyketide compounds have been used for the treatment of almost all important diseases; (2) The unique structure and synthesis me...

Claims

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Application Information

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IPC IPC(8): C07C327/30C07F7/18
CPCC07C327/30C07F7/1892Y02P20/55
Inventor 张有新杜晓行吴伟张俊勇
Owner SHANGHAI RUN BIOTECH CO LTD
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