Process for selectively oxidizing primary hydroxyl group of organic compounds and resin containing adsorbed catalyst for use therein

A technology for selective oxidation of organic compounds, applied in the direction of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, sugar compounds with non-sugar groups, etc., can solve adverse effects, inefficiencies, and undeveloped Issues such as primary hydroxyl

Inactive Publication Date: 2000-12-20
CHUGAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the catalyst usually appears in the reaction system in the form of a solution, cumbersome and inefficient steps (mixing with water, steaming, extraction with an organic solvent, etc.) are required to recover the catalyst, and a recovery device is also required, which brings some operational and cost issues
[0007] In addition, many amine oxides have adverse effects on the human body, so they must be handled with care
[0008] Therefore, a satisfactory method for the convenient and efficient oxidation of primary hydroxyl groups of organic compounds using amine oxides as catalysts has not been developed so far.

Method used

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  • Process for selectively oxidizing primary hydroxyl group of organic compounds and resin containing adsorbed catalyst for use therein
  • Process for selectively oxidizing primary hydroxyl group of organic compounds and resin containing adsorbed catalyst for use therein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] 150 mg of N-oxyl-2,2,6,6-tetramethylpiperidine (TEMPO) was added to 150 ml of water. Then 75 ml of synthetic polyacrylate resin "Diaion" HP2MG (Mitsubishi Chemical Industries) which had been previously washed and wetted with water was added thereto under stirring at room temperature. After stirring for 20 minutes, it was confirmed by gas chromatography (detection: FID, column: G-100 (40m), detection temperature: 150°C) that TEMPO in the aqueous solution was adsorbed by the resin at a rate of 98.0% or more. The resin with TEMPO adsorbed thereon was then filtered off to obtain about 75 ml of resin with TEMPO adsorbed thereon.

Embodiment 2

[0069]Dissolve 9.7 g of methyl-α-D-glucopyranoside in 150 ml of water. Under stirring, 5.3 g of anhydrous sodium carbonate, 2.0 g of sodium bromide and 75 ml of the TEMPO-adsorbed resin obtained in Example 1 above were added. The resulting mixture was kept at an internal temperature of 30°C or lower with stirring, and about 190 ml of an aqueous sodium hypochlorite solution containing 5% active chlorine was added dropwise. After stirring for 1.5 hours, by HPLC (detection: RI, UV 210 nm, column: Shodex SUGAR SH1011, column temperature: 25°C, mobile phase: 0.1% phosphoric acid aqueous solution; or RI, UV 210 nm, column: Aminex HPX-87H, Column temperature: 60°C, mobile phase: 0.1N sulfuric acid) proved that methyl-α-D-glucopyranoside had been converted into methyl-α-D-glucopyranoside uronic acid at a rate of 100%. After the above reaction was completed, it was confirmed by gas chromatography (detection: FID, column: G-100 (40m), detection temperature: 150° C.) that no TEMPO was e...

Embodiment 3

[0071] Dissolve 9.7 g of methyl-α-D-glucopyranoside in 150 ml of water. Under stirring, 8.0 g of anhydrous sodium carbonate, 2.0 g of sodium bromide and 150 ml of TEMPO were added. While maintaining the resulting mixture at an internal temperature of 30°C or lower with vigorous stirring, about 60 ml of an aqueous sodium hypochlorite solution containing 12% active chlorine was added dropwise. After stirring for 1.5 hours, it was proved by HPLC (detection: RI, UV 210 nm, column: Shodex SUGAR SH1011, column temperature: 25°C, mobile phase: 0.1% phosphoric acid aqueous solution) that methyl-α-D-glucopyranoside had been A rate of 100% was converted to methyl-α-D-glucopyranoside uronic acid. Subsequently, 75 ml of synthetic polyacrylate resin "Diaion" HP2MG (Mitsubishi Chemical Industries), which had been previously washed and wetted with water, was directly added to the liquid reaction mixture under stirring at room temperature, thereby allowing the resin to adsorb TEMPO in the li...

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Abstract

A method for selectively oxidizing the primary hydroxyl group of an organic compound which comprises reacting a resin having an amine oxide adsorbed thereon and an electrolytically oxidized product of a halogen-containing compound with the organic compound having the primary hydroxyl group.

Description

technical field [0001] The present invention relates to a resin having amine oxide adsorbed thereon which is used as a catalyst in the selective oxidation reaction of an organic compound having a primary hydroxyl group, a method for selectively oxidizing a primary hydroxyl group of an organic compound using the resin, and an amine oxide used in the oxidation reaction recycling method. The present invention also relates to a method for producing uronic acid derivatives such as glucuronic acid derivatives and a method for producing glucuronic acid or glucuronolactone. technical background [0002] Glucuronic acid, glucuronolactone and their derivatives are widely used as medicines. Industrially, in order to synthesize glucuronic acid derivatives used as intermediates in the synthesis of glucuronic acid and glucuronolactone, nitric oxide (nitric acid, etc.) is used as an oxidizing agent to selectively oxidize the starting materials (glucose derivatives, The primary hydroxyl g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02B01J31/08B01J31/40
CPCB01J31/0235B01J31/40B01J2231/70B01J31/08B01J31/006B01J31/0237
Inventor 越智清成藤崎勋高桥英德小里一友田中英树杉山宏
Owner CHUGAI PHARMA CO LTD
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