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Process for preparing D-proline

A technology of proline and proline refined salt, which is applied in the direction of organic chemistry, can solve the problems of low total yield, increased consumption, and difficulty in obtaining pure products, and achieve the effect of reducing costs and usage

Inactive Publication Date: 2004-12-22
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the following disadvantages: the total yield is low; in the resolution step, there will be entrainment and separation of diastereoisomers, resulting in a reduction in optical purity; adding a racemization step, the operation increases, and various aspects increased consumption
The Japanese Shiraiwa et al. have reported the process of preparing D-proline by asymmetric transformation method, but the consumption of raw materials and solvents is large, it is not easy to obtain pure products, and it has no practical significance in industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0024] The first step D-tartrate·D-proline salt preparation

[0025] Dissolve the mixture of 11.5g L-proline and 15.0g D-tartaric acid in 150.00mL organic acid, add 10-30% aliphatic aldehyde, stir at 80±5°C for 4 hours, cool to room temperature and then use Cool in an ice-water bath for 0.5 hour and filter. The solid was washed with absolute ethanol and dried to obtain 23.1 g of white crystals of D-proline D-tartrate, with a yield of 87.2%, [α] D 20 22.0°.

[0026] The crude salt was recrystallized with 95% ethanol to obtain 19.0g of refined salt with a yield of 82.3%, [α] D 20 24.0°.

[0027] Preparation of the second step D-proline

[0028] Dissolve 26.5 g of D-proline refined salt of D-tartrate obtained by the above recrystallization in methanol, slowly add ammonia gas under stirring at 20-65°C to make the solution weakly alkaline, stir at room temperature for 1 hour, and then cool to 5~ 10°C, filter and wash the solid with an appropriate amount of methanol for 1-2 t...

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Abstract

A process for preparing D-proline includes such steps as mixing L-proline with D-tartaric acid, dissolving in organic acid, adding catalyst, stirring at 80+ / -10 deg.c for 4-8 hr, cooling in ice water bath, filtering, washing with absolute alcohol, drying, recrystallizing in alcohol to obtain salt of D-tartaric acid. D-proline, dissolving it in methanol, stirring at 20-65 deg.c while adding aminating agent until the solution shows weak alkaline, stirring, cooling to 5-10 deg.c, filtering out ammonium D-tartarate, removing methanol from mother liquid, and recrystallizing.

Description

1. Technical field: [0001] The invention is a method for preparing chiral organic compounds, especially a method for preparing D-proline. 2. Background technology: [0002] D-amino acid is an important class of chiral reagents and chiral intermediates. At present, most of the production of D-amino acid is to prepare the racemate by synthetic method, and then carry out the resolution to obtain the optical isomer. Therefore, the resolution of racemic amino acids is an important step in the production of D-amino acids. [0003] One of the most commonly used separation methods for racemic amino acids is the chemical resolution method. Even if the racemic amino acid reacts with a chiral reagent to form diastereomers, they are separated by utilizing the differences in physical and chemical properties of the diastereomers. Amino acids contain both acidic groups and basic groups, and are amphoteric compounds. Therefore, the most convenient way is to make them react with asymmetric...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/16
Inventor 蒋立建邹建忠张征林谷传洲崔红雁仕翔鸣
Owner SOUTHEAST UNIV
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