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Process for preparing L-cysteic acid and its ester

A technology of sulfoalanine ester and sulfoalanine, which is applied in the field of medicine, can solve the problems of high temperature in reaction conditions, environmental pollution of waste liquid discharge, long reaction time, etc., and meet the requirements of simple production equipment and less side reactions , the effect of short reaction time

Inactive Publication Date: 2005-09-07
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Directly using liquid bromine as an oxidant is not only expensive, high cost, but also severely corroded, and there are also environmental pollution problems such as waste liquid discharge.
At present, there is also a synthesis method using dimethyl sulfoxide as an oxidant, but the reaction time is long, there are many impurities, and the purification is difficult
In addition, there are also those prepared by using peroxide as the oxidizing agent. The reaction conditions require high temperature and the operation is complicated.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 200 grams of L-cystine and 2500 milliliters of deionized water into a 5000 milliliter reaction flask, stir, then feed chlorine gas at 25° C., and absorb the tail gas with 5% NaOH aqueous solution. When the solution became transparent and clear, continue to pass chlorine gas for 30 minutes, and then continue to stir at room temperature for 3 hours. After the reaction was completed, the reaction mixture was concentrated to 600 ml, crystallized at 0° C., filtered, and dried to obtain 198 g (70.3%) of L-sulfoalanine.

[0016] L-sulfoalanine is characterized by:

[0017] Color and shape: white crystal

[0018] Melting point: 245-248°C

[0019] Specific rotation: +5.9(c5.1, H 2 O)

[0020] Infrared spectrum: The main characteristic bands are located at 3157, 2585, 1767, 1616, 1576, 1505, 1417, 1364, 1239, 1132, 1081, 1062and1029cm -1

[0021] Mass spectrum: (ESI(-)): 168(M-H) -

[0022] Proton NMR spectrum (600MHz, D 2 O, δin ppm and TMS as internal standard): δ4...

Embodiment 2

[0024] Add 100 grams of L-cystine and 1500 milliliters of anhydrous methanol into a 2500 milliliter reaction bottle, stir, then feed chlorine gas, and absorb the tail gas with 5% NaOH aqueous solution. After the L-cystine solid is completely dissolved, continue to pass Chlorine gas was introduced until the reaction solution was completely solidified, filtered, washed with ether, and dried to obtain 142 g (93.1%) of L-sulfoalanine methyl ester.

[0025] L-sulfoalanine methyl ester is characterized by:

[0026] Color and shape: white powder

[0027] Melting point: 220-224°C

[0028] Specific rotation: +17.3(c2.6, H 2 O)

[0029] Infrared spectrum: The main characteristic bands are located at 3177, 3023, 2919, 1748, 1595, 1496, 1441, 1424, 1373, 1334, 1290, 1272, 1179, 1139, 1101and1032cm -1

[0030] Mass Spectrum: (ESI(+)): 184(M+H) +

[0031] (ESI(-)): 182(M-H) -

[0032] Proton NMR spectrum (600MHz, D 2 O, δin ppm and TMS as internal standard): δ4.58(1H, dd, J=3.8, 7...

Embodiment 3

[0035] Add 100 grams of L-cystine and 1500 milliliters of n-hexanol in the 2500 milliliter reaction flask, stir, feed chlorine gas then, tail gas is absorbed with 5% NaOH aqueous solution, when L-cystine solid dissolves, continue to feed chlorine gas to The reaction solution became viscous solid again, filtered, the filtrate was discarded, the filter residue was dissolved with methanol and filtered to remove a small amount of insoluble matter, the filtrate was concentrated and crystallized to obtain 169 grams of L-sulfoalanine n-hexyl ester (yield 80.2%) .

[0036] L-sulfoalanine n-hexyl ester is characterized in that:

[0037] Color and shape: white crystal

[0038] Melting point: 194-196°C

[0039] Specific rotation: -4.0(c8.2, MeOH:H 2 O=1:5)

[0040] Infrared Spectrum: The main characteristic bands are located at 3470, 2595, 2860, 1745, 1602, 1535, 1469, 1421, 1397, 1376, 1341, 1222, 1150, 1090, 1070and1039cm -1

[0041] Mass Spectrum: (ESI(+)): 254(M+H) +

[0042]...

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Abstract

The invention discloses a process for preparing L-cysteic acid and L-cysteic acid ester, which is prepared from L- cysteine and chlorine as raw material through mixing L- cysteine with a predetermined amount of water or corresponding alcohol, letting in chlorine for oxidization, finally carrying out concentration or recrystallization to obtain the final product.

Description

[0001] 1. Field [0002] The invention belongs to the technical field of medicine. More specifically, it relates to a preparation method of a compound, and relates to a method for preparing L-sulfoalanine or L-sulfoalanine ester in water or alcohol by using L-cystine and chlorine gas as raw materials. 2. Background technology [0003] L-sulfoalanine is an important biochemical reagent, which has a wide range of physiological effects in animals and is increasingly used in medicine, cosmetics, detergents and other industries. It can be used as a raw material to synthesize anti-HIV (HIV I), Herpes Simplex I virus, coccus and bacillus drugs; polysulfoalanine can inhibit the proliferation of cancer cells without any side effects on uninfected cells; Amino acid hair conditioner can maintain hair elasticity and moisture, and sulfoalanine-containing styling agents and hair dyes can prevent hair damage, repair damaged hair and improve ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/18
Inventor 陶飞燕罗应刚魏其艳张国林
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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