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Preparation method of 2-chloro trityl chloride resin

A technology of chlorotrityl chloride resin and chlorotrityl alcohol, applied in the field of preparation of 2-chlorotrityl chloride resin, can solve the problems of difficult and complicated reaction operation conditions 2-CTC resin, and achieves The effects of excellent swelling properties and amino acid loading rate, simple preparation and easy operation

Inactive Publication Date: 2010-09-22
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the preparation method steps of preparing 2-CTC resin on the basis of polystyrene carrier are more complicated and must use organometallic reagents, and Orosz G et al. reported in Tetrahedron Letters 1998 39 volumes 3241-3242 pages that polystyrene Resin and benzoyl chloride were subjected to Friedel-Crafts acylation reaction to obtain benzophenone-derived polymers, and then organolithium reagents were used to convert benzophenone-derived polymers into trityl chloride polymers; Choi MKW et al. in Tetrahedron 2004 60 pages 3903-3907 reported the preparation method of 2-CTC resin by polymerizing tritylated monomers, which requires the use of Grignard reagents
Therefore, the reaction operating conditions, reagent costs and waste disposal of organometallic reagents may become difficult problems in the large-scale production of 2-CTC resins.
At present, there are no patents and literature reports on the preparation method of 2-CTC resin in China.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 10.825g (0.05mol) of 2-chlorobenzophenone and 14.075g (0.05mol) of phosphorus pentachloride into a 100mL reaction bottle, heat the mixture at 100-110°C for 8h, and wait for the mixture to Cool to room temperature, slowly add 10mL acetone and 15mL water under ice bath conditions, recover the organic layer after fully shaking, wash twice with 15mL water and dry with anhydrous magnesium sulfate for 8h, and the filtrate is concentrated under reduced pressure to obtain yellow oily liquid 1-chloro -2-Dichlorobenzylbenzene (DCPB). The purity of the product by reverse-phase high-performance liquid chromatography was 80.75%. The molecular weight of the product by mass spectrometry was 270.0, and the structure of the product by 600M proton nuclear magnetic resonance was correct.

Embodiment 2

[0025] Weigh 1.00g DVB-PS (cross-linking degree 3.0%, particle size 400-800 mesh) to swell in 20mL chloroform, add aluminum chloride (2.037g, 15.0mmol) / nitrobenzene (5mL) solution, and then DCPB (10.90 g) / chloroform (5 mL) solution was added slowly, and the mixed solution was stirred and reacted at room temperature for 10 h. After the reaction was completed, the mixture was cooled to 0° C., and 5 mL of methanol, 5 mL of water, and 5 mL of 1M hydrochloric acid solution were added to terminate the reaction. Collect the resin after filtration, wash it successively with 20mL methanol, 20mL dichloromethane (twice), and 20mL tetrahydrofuran (twice), and obtain a yellow resin after vacuum drying. The structure of the product is correct according to infrared spectroscopy, and the swelling properties of 2-CTA resin are tested by sampling It is 2.24g (DCM) / g (resin), 3.68g (DMF) / g (resin).

[0026] Weigh 1.60g of 2-CTA resin and suspend in 15mL of chloroform, slowly add 0.74mL (10.0mmo...

Embodiment 3

[0029] Weigh 2.00g DVB-PS (cross-linking degree 1.0%, particle size 200-400 mesh) to swell in 20mL dichloromethane, add aluminum chloride (3.394g, 25.0mmol) / nitrobenzene (10mL) solution, and then DCPB (12.42g) / dichloromethane (5mL) solution was added slowly, and the mixed solution was stirred and reacted at room temperature for 6h. After the reaction was completed, the mixture was cooled to 0° C., and 5 mL of acetone, 5 mL of ethanol, and 5 mL of 1M hydrochloric acid solution were added to terminate the reaction. The resin was collected after filtration, washed successively with 20 mL of methanol, 20 mL of chloroform (twice), and 20 mL of tetrahydrofuran (twice), and dried in vacuum to obtain a yellow resin. The structure of the product was correct according to infrared spectroscopy. The swelling properties of the 2-CTA resin were sampled and detected to be 7.94g (DCM) / g (resin) and 5.09g (DMF) / g (resin).

[0030] Weigh 3.130g of 2-CTA resin and suspend in 30mL of N,N-dimethy...

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Abstract

The invention discloses a preparation method of 2-chloro trityl chloride resin in the fields of medicine, biological chemistry and chemical engineering, which comprises the following steps that: 2-chlorobenzophenone is adopted as the raw material to synthesize 1-chlorine-2- dichloro-diphenyl benzene, and the 1-chlorine-2- dichloro-diphenyl benzene is chemically coupled with low cross-linked polystyrene (PS) white balls to obtain the 2-chloro trityl chloride (2-CTC) resin. The method overcomes the defects of a traditional 2- chloro trityl chloride resin preparation method that the steps are complicated and organic metal reagent must be used, is simple and feasible, does not need to use the organic metal reagent, the uploading level of the first amino acid, swelling property and peptide solid-phase synthesis efficiency of the prepared 2-CTC resin are better than those of similar commodities 2-CTC resin, and the mass quality is stable, the repeatability is good and the industrial production is easy.

Description

technical field [0001] The present invention relates to the preparation method of 2-chlorotrityl chloride resin in the fields of medicine, biochemical industry and chemical engineering. Process for the preparation of high 2-chlorotrityl chloride resins. Background technique [0002] In the field of peptide synthesis, the solid-phase synthesis method has the advantages of simple operation, few by-products, and high purification efficiency. in production. In Solid-phase Peptide Synthesis (SPPS), the choice of solid-phase carrier is a crucial step, which directly affects the yield and purity of the final target peptide, and then affects the economic efficiency of the entire synthesis. 2-Chlorotrityl chloride (2-chlorotrityl chloride, 2-CTC) resin is a commonly used carrier resin in SPPS, because its reaction conditions are milder than other resins, it can effectively inhibit racemization and diketopyridine Occurrence of side reactions such as oxazine formation and high produ...

Claims

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Application Information

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IPC IPC(8): C08F8/18C08F12/08
Inventor 苏志国马光辉李鹏张竞
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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