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Preparation method of tryptophan ester hydrochloride

A tryptophan and hydrochloride technology, applied in organic chemistry and other directions, can solve the problems of poor atomic economy, high activity and violent reaction, and achieve the effects of low cost of raw materials, less discharge of three wastes, and simple post-processing

Active Publication Date: 2018-03-13
MAANSHAN DEHONG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method has higher yield and no by-products, due to SOCl 2 High activity, violent reaction, must be operated at low temperature, the reaction atom economy is poor, and SOCl 2 High toxicity, not conducive to large-scale industrial production

Method used

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  • Preparation method of tryptophan ester hydrochloride
  • Preparation method of tryptophan ester hydrochloride
  • Preparation method of tryptophan ester hydrochloride

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Experimental program
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Embodiment 1

[0027] Embodiment 1, a kind of preparation method of tryptophan ester hydrochloride, take tryptophan and methanol as raw material, carry out following steps successively:

[0028] (1) Initial response:

[0029] ①. Put 20.4g (0.1mol) tryptophan, 30ml dichloroethane and 1.29g (0.01mol) DIPEA into a 250ml three-necked flask, feed hydrogen chloride gas at a rate of 1.25ml / s (within the reaction time of 0.5h Hydrogen chloride gas has been introduced at this rate), and the reaction was carried out at room temperature for 0.5h.

[0030] ②, after that, put 4.16g (0.13mol) methanol into the above-mentioned three-necked flask, and feed hydrogen chloride at 0.05ml / s (the hydrogen chloride gas has been fed at this rate during the reaction time of 3h), and under reflux conditions, distill out the water-containing Ethylene dichloride (that is, the mixed solution steamed out of the process of azeotropic band water), and add anhydrous ethylene dichloride dropwise to the reaction system at th...

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Abstract

The invention discloses a synthesizing method for tryptophan ester hydrochloride. The synthesizing method includes the steps that firstly, organic amine serves as catalysts, in proper solvents, tryptophan and hydrogen chloride generate tryptophan hydrochloride; secondly, the tryptophan hydrochloride and ester are esterified at the backflow temperature, generated water is taken away in an azeotropy mode, an esterification reaction is promoted, and after the reaction is completed, the tryptophan ester hydrochloride as the target product is obtained through postprocessing processes such as filtering, low-boiling-point substance low-pressure removing and recrystallization. Mother liquid obtained after recrystallization is repeatedly used indiscriminately, and the number of repeating times is larger than five. The synthesizing method has the advantages that the raw material cost is low, the conversion rate is high, postprocessing is simple, chlorinating agents such as thionyl chloride are not required, and three-waste discharging is less; the synthesizing method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of organic compound tryptophan ester hydrochloride. Background technique [0002] The main synthetic method of tryptophan ester hydrochloride: (Der Pharma Chemica, 2011,3 (3): 354-363) adopts tryptophan and methanol, in SOCl 2 The method for synthesizing tryptophan methyl ester hydrochloride under the effect of. The specific steps are: tryptophan (0.1mol) is added dropwise to SOCl 2 (0.05mol+excess 30%) and methanol (100mL), react at reflux temperature of 60-70°C for 7h, and then remove excess SOCl under reduced pressure 2 and a solvent (methanol, which is used both as a solvent and as a reaction material), and treated with 20 mL of ether at 0° C. to obtain a crude product until the excess dimethylsulfite was completely removed. Dry the product under vacuum, dissolve the product with 15-20 mL of hot methanol, recrystallize at 0°C, then wash with a mixture of diethyl ether and methanol (5:1 by volume), th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/20
CPCC07D209/20
Inventor 祁超高锐葛新杨建平
Owner MAANSHAN DEHONG BIOTECH