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A method for preparing fmoc-tyr(tbu)-oh

A fmoc-tyr-or, solid technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbamic acid derivatives, etc., can solve the problems of easy formation of explosive mixtures, potential safety hazards, poor safety, etc., and shorten production Steps, low cost, and the effect of improving production efficiency and yield

Active Publication Date: 2022-06-21
成都郑源生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although the method is simple in steps, it still needs to use isobutene when introducing tert-butyl. Isobutene is a gas at normal temperature and pressure, which is inconvenient to operate, and it is easy to form an explosive mixture if it leaks into the air, which has certain safety hazards. Therefore, this method The method is not safe and needs further improvement

Method used

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  • A method for preparing fmoc-tyr(tbu)-oh
  • A method for preparing fmoc-tyr(tbu)-oh
  • A method for preparing fmoc-tyr(tbu)-oh

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Weigh and add 18 grams of L-Tyr (tyrosine) and 100 ml of methanol into the reaction flask, and add SOCl dropwise with stirring. 2 (thionyl chloride) 120ml, reflux reaction. When TLC (thin layer chromatography) detected that there was no L-Tyr (tyrosine) in the reaction system, the reaction was completed. The reaction solution after the above reaction was concentrated in vacuo to a volume of 20 ml, and 100 ml of petroleum ether was added to precipitate a white solid. Centrifuged and dried to obtain 19.2 g of white solid with a yield of 95.3%.

[0054] 19.2 grams of Tyr-OCH will be obtained 3 Add HCl to 160ml acetone and 40ml water, adjust pH=8-9 with sodium carbonate, add 33.7 g Fmoc-OSu, react at room temperature for 8 hours, adjust pH=2-3 with 1M dilute hydrochloric acid, and precipitate a white solid Fmoc-Tyr- OCH 3 , filtered and dried to obtain 39.8 g of white solid with a yield of 95.4%.

[0055] 39.8 g of Fmoc-Tyr-OCH will be obtained 3 , added to 500ml of te...

Embodiment 2

[0058] Weigh and add 18 g of L-Tyr (tyrosine) and 100 ml of ethanol into the reaction flask, and add SOCl dropwise with stirring. 2 (thionyl chloride) 120ml, reflux reaction. When TLC (thin layer chromatography) detected that there was no L-Tyr (tyrosine) in the reaction system, the reaction was completed. The reaction solution after the above reaction was concentrated in vacuo to a volume of 20 ml, and 100 ml of petroleum ether was added to precipitate a white solid. Centrifuged and dried to obtain 19.8 g of white solid with a yield of 94.7%.

[0059] Add 19.8 g of Tyr-OEt·HCl to 160 ml of acetone and 40 ml of water, adjust pH=8-9 with sodium carbonate, add 33.7 g of Fmoc-OSu, react at room temperature for 8 hours, adjust pH=2-3 with 1M dilute hydrochloric acid , a white solid Fmoc-Tyr-OEt was precipitated, filtered and dried to obtain 40.1 g of a white solid with a yield of 93.2%.

[0060] The obtained 40.1 g of Fmoc-Tyr-OEt was added to 500 ml of tert-butyl acetate and 10...

Embodiment 3

[0063] Weigh and add 180 g of L-Tyr (tyrosine) and 1000 ml of methanol to the reaction flask, and add SOCl dropwise with stirring. 2 (thionyl chloride) 1200ml, reflux reaction. When TLC (thin layer chromatography) detected that there was no L-Tyr (tyrosine) in the reaction system, the reaction was completed. The reaction solution after the above reaction was concentrated in vacuo to a volume of 20 ml, and 100 ml of petroleum ether was added to precipitate a white solid. Centrifuged and dried to obtain 191 g of white solid with a yield of 95.0%.

[0064] 191 grams of Tyr-OCH will be obtained 3 Add HCl to 1600ml acetone and 400ml water, adjust pH=8-9 with sodium carbonate, add 337 grams of Fmoc-OSu, react at room temperature for 8 hours, adjust pH=2-3 with 1M dilute hydrochloric acid, and precipitate a white solid Fmoc-Tyr- OCH 3 , filtered, and dried to obtain 398 g of white solid, with a yield of 95.4%.

[0065] The resulting 398 g of Fmoc-Tyr-OCH 3 , added to 5000ml of t...

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Abstract

The invention relates to a method for preparing Fmoc-Tyr(tBu)-OH, which belongs to the technical field of pharmaceutical intermediate chemical industry. The technical problem solved by the present invention is to provide a method for preparing Fmoc-Tyr(tBu)-OH with good safety. The method comprises the following steps: a. After the mixed reaction of Fmoc-Tyr-OR solid, tert-butyl acetate, perchloric acid and tert-butanol, adjust pH=5~6, precipitate solid, filter, wash and dry to obtain Fmoc -Tyr(tBu)-OR solid; wherein, the R is C1-C4 alkyl; b, Fmoc-Tyr(tBu)-OR solid hydrolysis to obtain Fmoc-Tyr(tBu)-OH product. The method of the present invention is improved on the existing synthetic route, no isobutene is added when the tert-butyl group is introduced, the operation is simple and controllable, the safety is good, the cost is low, the production steps can be effectively shortened, and the production efficiency and yield can be improved. Adapt to modern industrial production.

Description

technical field [0001] The invention relates to a method for preparing Fmoc-Tyr(tBu)-OH, which belongs to the technical field of pharmaceutical intermediate chemical industry. Background technique [0002] Fmoc-Tyr(tBu)-OH is fluorenemethoxycarbonyl-oxy-tert-butyl-tyrosine, is a chemical intermediate, commonly used in peptide synthesis, its structural formula is: [0003] [0004] Patent CN103833593A discloses a preparation method of N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-tyrosine, which first reacts to generate Tyr-OMe·HCl, and then reacts with benzyl chloroformate Prepare Z-Tyr-OMe, then pass isobutylene to prepare Z-Tyr(tBu)-OMe, then saponify to generate Z-Tyr(tBu), then hydrogenolysis to prepare Tyr(tBu), and finally react to generate Fmoc-Tyr(tBu) -OH. The method has long steps, low yield and low production efficiency, and uses the explosive gas isobutene, has poor safety, and is not suitable for modern industrial production. [0005] Li Xin et al. disclos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C269/06C07C271/22
CPCC07C269/06C07C2603/18C07C271/22
Inventor 潘俊锋张东海付若彬郑征
Owner 成都郑源生化科技有限公司
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