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Preparation method for R-ortho-chloromandelic acid and acyl compound thereof

A technology of o-chloromandelic acid and compounds, applied in the field of preparation of optically pure chiral compounds and their derivatives, to achieve the effects of overcoming low product yield, environmental friendliness and high selectivity

Inactive Publication Date: 2015-02-18
王同俊
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AI Technical Summary

Problems solved by technology

In the process of splitting and preparing R-o-chloromandelic acid and preparing R-o-chloromandelic acid acyl compounds, lipase and acidic resin are used as racemization catalyst combination for dynamic kinetic resolution, which not only overcomes the problem of low product yield problem, and ensure that the catalyst is cheap and easy to obtain, can be reused, and is easy to realize industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0008] 1) Preparation of acyl donor p-chlorophenol ester

[0009] Add 500ml of dichloromethane to a 1000ml round bottom flask. Then add 128g (1mol) of p-chlorophenol, 72g (1.2mol) of acetic acid, 247.5g (1.2mol) of DCC, and 2.44g (0.02mol) of DMAP. Stir at room temperature for 10 hours, and detect the disappearance of p-chlorophenol by pointing the plate, then the reaction ends. The solution was filtered, concentrated, and then passed through the column to obtain 156.9 g of pure p-chlorophenol acetate, with a yield of 92.3%.

[0010] Other p-chlorophenol propionate, p-chlorophenol n-butyrate, p-chlorophenol n-valerate etc. can also be prepared according to this example.

[0011] 2) Preparation of R-O-acetyl o-chloromandelic acid by dynamic kinetic resolution

[0012] Add 250ml of toluene to a 500ml Erlenmeyer flask, then add 92.8g (0.5mol) of racemic o-chloromandelic acid, 93.5g (1.1mol) of p-chlorophenol acetate, 3g of Novozym, and 6g of acidic resin CD550. After the addi...

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Abstract

The invention discloses a preparation method for an R-ortho-chloromandelic acid and an acyl compound thereof. According to the preparation method, racemic chlomandelic acid is adopted as the raw material, lipase is adopted as a biological separation catalyst, acidic resin is adopted as a racemic catalyst, p-chlorobenzenethiol phenolic ester is adopted as the acyl donor to carry out the dynamic kinetic resolution to obtain the acyl compound of the R-ortho-chloromandelic acid; LiOH is adopted for hydrolysis to obtain the R-ortho-chloromandelic acid. The preparation method is moderate in reaction condition, environment-friendly, high in product yield and high in selectivity, the adopted racemic catalyst is low in cost and easy to obtain, so that the preparation method has quite high application value in industrial production.

Description

technical field [0001] The invention relates to a preparation method of optically pure chiral compounds and derivatives thereof, in particular to a preparation method of dynamic dynamic resolution of optically pure R-o-chloromandelic acid and its acyl compounds. Background technique [0002] As an important chiral drug intermediate for the synthesis of clopidogrel, R-o-chloromandelic acid is an important derivative of mandelic acid. At present, the preparation of R-o-chloromandelic acid is still mainly based on the resolution method. The separation of racemates to obtain chiral substances, especially the resolution of diastereomeric salts to obtain single-configuration enantiomers, is still the main method. However, the resolution method requires expensive chiral resolution reagents, and undesired by-product enantiomers will be obtained after resolution. The atom economy is not high. Even if repeated recycling and regeneration, by-products will still be formed, resulting in ...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P7/42
Inventor 王同俊
Owner 王同俊
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