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Preparation method of 7-ethyl chrotol

A technology of ethyl tryptol and ethyl indole, which is applied in the field of preparation of 7-ethyl tryptol, can solve the problems of high production cost, low yield, long process route, etc., and achieves improved operational safety and simplified production operation. , the effect of shortening the process route

Pending Publication Date: 2021-11-19
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] document Heterocycles, 2003, 60 (5) 1095-1110 then adopts the active precursor 3-ethoxytetrahydrofuran of 2,3-dihydrofuran as 4-hydroxyl The donor of butyraldehyde also cannot avoid the problem of high production cost:
[0031] 1. The process route is long, and the final product involves vacuum fractionation operation, which is cumbersome and makes the overall yield low
[0032] 2. The target product is prepared by the Fischer Indole synthesis method under strong acidic conditions. The resulting product has more impurities, is difficult to purify, and has a lower yield
[0033] 3. The process needs to use a large amount of acetonitrile, DMF, DMAc, isobutanol and other non-environmentally friendly organic solvents or expensive solvents, and the solvent recovery rate is low
[0034] 4. The process uses highly dangerous lithium aluminum hydride and highly toxic KCN, which makes the operation less safe.
[0035] 5. Using slightly higher priced 2,3-dihydrofuran or its active precursor 3-ethoxytetrahydrofuran as the donor of 4-hydroxybutyraldehyde, resulting in higher production costs
[0036] In summary, the current preparation method of 7-ethyltryptol has many deficiencies in terms of safe process, cumbersome operation, low yield, and high production cost. , high purity, low production cost suitable for industrialized production of 7-ethyl tryptophan reaction route is still a problem to be solved at present

Method used

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  • Preparation method of 7-ethyl chrotol
  • Preparation method of 7-ethyl chrotol
  • Preparation method of 7-ethyl chrotol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] At room temperature, add 7-ethylindole (14.52g, 0.1mol) and potassium carbonate (16.58g, 0.12mol) into N,N-dimethylformamide (150ml), and add sulfite Ethyl ester (19.37g, 0.22mol), after the addition was completed, the temperature was controlled at 110-115°C until the reaction was completed, the reaction solution was cooled to room temperature and filtered, the filtrate was added with dichloromethane (100ml), and the organic phase was obtained by liquid separation. Washed with saturated brine (100ml×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the target product with a yield of 98.7% and a purity of 99.92% by HPLC.

Embodiment 2

[0060] At room temperature, add 7-ethylindole (14.52g, 0.1mol) and potassium carbonate (13.82g, 0.1mol) into 1.4-dioxane (150ml), and add ethylene carbonate ( 19.37g, 0.22mol), the addition is completed, the temperature is controlled at 90-100°C until the reaction is completed, the reaction solution is cooled to room temperature and filtered, the filtrate is added with dichloromethane (100ml), the organic phase is separated, and the organic phase is washed with saturated saline (100ml×2) washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the target product, with a yield of 94.6% and a HPLC purity of 99.86%.

Embodiment 3

[0062] At room temperature, add 7-ethylindole (14.52g, 0.1mol) and potassium carbonate (27.64g, 0.2mol) into xylene (150ml), and add ethylene carbonate (19.37g, 0.22 mol), the addition is completed, the temperature is controlled at 115-120 ° C until the reaction is over, the reaction solution is cooled to room temperature and filtered, the filtrate is added with dichloromethane (100ml), the liquid is separated to get the organic phase, and the organic phase is washed with saturated brine (100ml×2 ), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the target product. The yield was 93.9%, and the HPLC purity was 99.76%.

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Abstract

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 7-ethyl chromone, which comprises the following steps: reacting 7-ethyl indole serving as a raw material with ethylene carbonate under the action of alkali to synthesize 7-ethyl chromone; the hydroxyethyl ethylene carbonate reagent product introduced in the method is carbon dioxide, the method is clean and environmentally friendly, post-treatment is convenient, dangerous chemical reagents are not used, the reaction is milder, economical and environmentally friendly, the yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of 7-ethyl tryptophan. Background technique [0002] Etodolac (Etodolac) is a powerful non-steroidal anti-inflammatory analgesic, used for the treatment of rheumatoid arthritis, rheumatoid arthritis and osteoarthritis embolism, with good tolerance, mild side effects, Strong analgesic effect and other characteristics, this product has few gastrointestinal adverse reactions, especially suitable for elderly patients. The drug was developed by AHP Wyeth-Ayesrt in the United States and first launched in the UK in 1985. Its chemical structure is as follows: [0003] [0004] 7-Ethyltryptol, as a key intermediate in the synthesis of etodolac, directly affects the production, market supply and quality of the drug. Its chemical structural formula is as follows: [0005] [0006] The preparation method about 7-ethyl tryptophan reported at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12
CPCC07D209/12Y02P20/55
Inventor 王亚青鲍广龙刘忠
Owner LUNAN PHARMA GROUP CORPORATION
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