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Method for preparing phthaloylamino acid

A technology of phthalyl amino acid and phthalic anhydride, which is applied in the field of preparation of phthalyl amino acid, can solve problems such as bumping, and achieve mild reaction effect

Inactive Publication Date: 2012-07-25
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when this method is applied to the preparation of phthalyl amino acids other than phthalyl phenylalanine, there will be bumping

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Embodiment 1, prepares phthaloylglycine

[0013] In the first step, add 0.01 mole of phthalic anhydride, 0.01 mole of glycine and 1 gram of 4A molecular sieve to 0.04 mole of pyridine, heat the reactor to 100°C, react until glycine is completely dissolved, and keep warm for 0.5h;

[0014] In the second part, filter while it is hot, add the filtrate to 0.6 mole of distilled water, cool to 5°C in an ice bath, adjust the pH to 2-3 with 37% hydrochloric acid in an ice bath, cool to 5°C in an ice bath, and filter the obtained residue with volume Recrystallization from a 50% ethanol solution yielded 1.87 g of white crystals, with a yield of 91%. 1 HNMR (DMSO), δ H : 12.1 (1H), 7.7-7.8 (4H), 4.8 (1H).

Embodiment 2

[0015] Embodiment 2, preparation phthalyl L-alanine

[0016] In the first step, add 0.01 mole of phthalic anhydride, 0.01 mole of L-alanine and 1.5 grams of 4A molecular sieve to 0.08 mole of pyridine, heat the reactor to 80°C, and react until L-alanine is completely dissolved Keep warm for 1h;

[0017] The second step is to filter while it is hot, add the filtrate to 0.8 mole of distilled water, cool to 5°C in an ice bath, adjust the pH to 2 to 3 with 37% hydrochloric acid by mass fraction, cool to 5°C in an ice bath, and filter the resulting residue with volume 2.01 g of white crystals were obtained by recrystallization from a 50% ethanol solution, with a yield of 92%. 1 HNMR (DMSO), δ H : 12.2(1H), 7.7-7.8(4H), 4.8(1H), 1.5(3H).

Embodiment 3

[0018] Embodiment 3, preparation of phthaloyl L-glutamic acid

[0019] In the first step, add 0.01 mole of phthalic anhydride and 0.01 mole of L-glutamic acid to 0.16 mole of pyridine, heat the reactor to 115.3°C, react until L-glutamic acid is completely dissolved, and keep warm for 1 hour;

[0020] The second step is to filter while it is hot, add the filtrate to 1.2 moles of distilled water, cool to 5°C in an ice bath, adjust the pH to 2 to 3 with 37% hydrochloric acid by mass fraction, cool to 5°C in an ice bath, and filter the resulting residue with volume 2.29 g of white crystals were obtained by recrystallization from a 50% ethanol solution, with a yield of 83%. 1 HNMR (DMSO), δ H : 12.0(1H), 12.3(1H), 7.8~7.9(4H), 4.8(1H), 2.2~2.4(4H).

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Abstract

The invention relates to a method for preparing phthaloylamino acid, which comprises the following steps: 1. adding Y mol of phthalic anhydride and Z mol of amino acid into X mol of pyridine, then heating a reactor to the temperature of 80 to 115.3 DEG C, reacting until the amino acid is completely dissolved, and then preserving heat for 0.2 to 1 hour, wherein Y equals to nZ, X is not less than 4Y, and the n is the quantity of amino groups in a single molecule of the amino acid; 2. separating out the phthaloylamino acid. In the method for preparing the phthaloylamino acid of the invention, the heating temperature is 80 to 115.3 DEG C, the pyridine is used as a solvent and a catalyst, the reaction is mild, and no bumping phenomenon exists.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing phthalyl amino acid. Background technique [0002] Marguerite Fling etc. reported in J.Am.Chem.Soc., 1947,69 (10) by the solid-phase reaction synthesis of phthalyl amino acid by equivalent phthalic anhydride and amino acid, this method is at 140 ℃-190 Melt phthalic anhydride at ℃, then add amino acid to react until the bubbles disappear. The above method includes the preparation of phthaloyl D-valine, phthaloyl L-valine, phthaloyl D-leucine and phthaloyl L-leucine. [0003] However, the method reported by Marguerite Fling requires strict conditions such as high temperature, and the reaction is violent, and it is not easy to control the reaction process. Such conditions are not of high industrial interest as they are environmentally unfriendly and have high reactor requirements and tend to racemize amino acids and products. [0004] Organic syntheses, co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48
Inventor 尹大伟陈昫刘玉婷陈丹周英杨帆
Owner SHAANXI UNIV OF SCI & TECH