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A kind of preparation method of n-p-aminobenzoyl-l-glutamic acid

A technology of p-aminobenzoyl and p-nitrobenzoic acid, applied in the field of preparation of N-p-aminobenzoyl-L-glutamic acid, which can solve the inconvenience of industrial production, unsatisfactory yield, long reaction time, etc. problems, to achieve the effect of easy operation, mild reaction and mild reaction conditions

Active Publication Date: 2018-02-27
ZHEJIANG ESIGMA BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the preparation process of this method, a large amount of sulfur dioxide gas and solid waste iron sludge are produced, which is not conducive to environmental protection; the reaction time is long and the yield is not ideal, which brings inconvenience to industrial production

Method used

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  • A kind of preparation method of n-p-aminobenzoyl-l-glutamic acid
  • A kind of preparation method of n-p-aminobenzoyl-l-glutamic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Preparation of ethylene dichloride solution of p-nitrobenzoyl chloride

[0026] Add 16.71g (0.1mol) of p-nitrobenzoic acid, 67g of dichloroethane, and 0.29g (0.004mol) of DMF into a reaction vessel with a tail gas absorption device, raise the temperature to 40°C, and slowly add BTC / C 2 h 4 Cl 2 Solution 15.5ml, dropwise reflux reaction for 1 hour, concentrated under reduced pressure to about 1 / 3 of the original volume, to recover the solvent and remove hydrogen chloride, the residue is 32g of dichloroethane solution of p-nitrobenzoyl chloride, HPLC The purity of the target substance was determined to be 57.81%.

[0027] (2) Preparation of N-p-nitrobenzoyl-L-glutamic acid

[0028] Add 18.73 g (0.11 mol) of sodium glutamate and 75 g of water into the reaction vessel, adjust the pH to 8 with 1 mol / L aqueous sodium hydroxide solution under stirring, and slowly add 28.31 g of the mixture obtained in step (1) dropwise at 0°C. The dichloroethane solution of nitrobenzoy...

Embodiment 2

[0032] (1) Preparation of ethylene dichloride solution of p-nitrobenzoyl chloride

[0033] Add 16.71g (0.1mol) of p-nitrobenzoic acid, 83.6g of solvent dichloroethane, and 0.22g (0.003mol) of DMF into a reaction vessel with a tail gas absorption device, raise the temperature to 42°C, and slowly add BTC / C 2 h 4 Cl 2 Solution 10ml, dropwise reflux reaction for 1.5 hours, concentrated under reduced pressure to about 1 / 3 of the original volume, to recover the solvent and remove hydrogen chloride, the residue is 31.1g of dichloroethane solution of p-nitrobenzoyl chloride, HPLC The purity of the target substance was determined to be 58.56%.

[0034] (2) Preparation of N-p-nitrobenzoyl-L-glutamic acid

[0035] Add 18.73 g (0.11 mol) of sodium glutamate and 75 g of water into the reaction vessel, adjust the pH to 8.5 with 1 mol / L aqueous sodium hydroxide solution under stirring, and slowly add 29.7 g of the mixture obtained in step (1) dropwise at 3°C. The dichloroethane solutio...

Embodiment 3

[0039] (1) Preparation of ethylene dichloride solution of p-nitrobenzoyl chloride

[0040] Add 16.71g (0.1mol) of p-nitrobenzoic acid, 100.3g of dichloroethane, and 0.37g (0.005mol) of DMF into a reaction vessel with a tail gas absorption device, raise the temperature to 45°C, and slowly add BTC / C 2 h 4 Cl 2 Solution 12ml, dropwise reflux reaction for 2 hours, concentrated under reduced pressure to about 1 / 3 of the original volume, to recover the solvent and remove hydrogen chloride, the residue is 32g of dichloroethane solution of p-nitrobenzoyl chloride, determined by HPLC The purity of the target object was 57.23%.

[0041] (2) Preparation of N-p-nitrobenzoyl-L-glutamic acid

[0042] Add 18.73 g (0.11 mol) of sodium glutamate and 75 g of water to the reaction vessel, adjust the pH to 9 with 1 mol / L aqueous sodium hydroxide solution under stirring, and slowly add 29.7 g of the mixture obtained in step (1) dropwise at 5°C. The dichloroethane solution of nitrobenzoyl chlor...

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Abstract

The invention provides a preparation method of N (4-aminobenzoyl)-L-glutamic acid. According to the method, p-nitrobenzoic acid is taken as a raw material, BTC / C2H4Cl1 is taken as an acylating chlorination agent, DMF (dimethyl formamide) is added to serve as an initiator, and p-nitrobenzoyl chloride is prepared through reaction at a reflux temperature; p-nitrobenzoyl chloride and sodium glutamate have condensation, and N-(4-nitrobenzoyl)-L-glutamic acid is prepared; N-(4-nitrobenzoyl)-L-glutamic acid is reduced by Pd / C / HCO2NH4, and N (4-aminobenzoyl)-L-glutamic acid is prepared. The preparation method has mild reaction conditions and is simple in process, easy to operate and suitable for industrial production; few three wastes are generated, and a product has high purity and high yield.

Description

technical field [0001] The invention relates to a preparation method of N-p-aminobenzoyl-L-glutamic acid, belonging to the technical field of fine chemicals. Background technique [0002] N-(4-Aminobenzoyl)-L-glutamic acid [N-(4-Aminobenzoyl)-L-glutamic acid], also known as p-aminobenzoyl glutenic acid, its structural formula is as follows: [0003] [0004] N-p-aminobenzoyl-L-glutamic acid is an intermediate in the synthesis of anti-anemia drug folic acid. The currently known process for producing N-p-aminobenzoyl-L-glutamic acid is: p-nitrobenzoic acid is used as a raw material, and thionyl chloride is used as an acid chloride reagent to prepare p-nitrobenzoyl chloride , and then condensed with glutamic acid and reduced by iron powder to obtain the target product. During the preparation process of this method, a large amount of sulfur dioxide gas and solid waste iron sludge are produced, which is not conducive to environmental protection; the reaction time is long and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/36C07C231/12
CPCC07C201/12C07C231/02C07C231/12C07C205/57C07C233/83C07C237/36
Inventor 吴中华张小朋陈贵才徐天华何奇雷闻鸣张丽佳
Owner ZHEJIANG ESIGMA BIOTECH CO LTD
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