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A technology of acetyl and carnosine, applied in the field of preparation of N-acetyl-L-carnosine, can solve the problems of complex process, troublesome processing, low yield and the like, and achieve the effects of high HPLC purity, short synthesis route and cost reduction
Active Publication Date: 2016-04-06
HUBEI HUNTIDE BIOTECH
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The limitation of this method is that special highly active esters need to be prepared, which are currently unavailable in the market, and the process is complicated, so it is not suitable for industrial production.
[0008] Based on the above existing technologies, it is found that the current preparation of N-acetyl-L-carnosine is based on L-carnosine as its raw material, the price of raw materials is high, and the post-processing is troublesome due to low yield. It is necessary to obtain N-acetyl-L-carnosine by strong acid resin , the purity of the N-acetyl-L-carnosine obtained is low, so the difficulty of industrialization is relatively large
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Embodiment 1
[0036] Preparation of N-acetyl-β-alanine (I)
[0037] In a 250mL reaction flask, add 180mL of chloroform, 30g of β-alanine (0.337mol), 37.8g of acetic anhydride (0.371mol), raise the temperature to 60°C, and react for 5 hours. The sampled ninhydrin does not develop color, and the temperature is lowered to 4°C , stirred for 1 hour, suction filtered to obtain a solid, and dried to obtain 42 g of product (I), the yield was 95.4%, and the HPLC purity was ≥99.3%.
Embodiment 2
[0039] Preparation of N-acetyl-β-alanine (I)
[0040] In a 500mL reaction flask, add 360mL of dichloromethane, 60g of β-alanine (0.674mol), 48.5g of acetic acid (0.808mol), raise the temperature to 45°C, and react for 3 hours. The sampled ninhydrin does not develop color, and the temperature is lowered to 4 ℃, stirred for 1 hour, filtered to obtain a solid, and dried to obtain 82.5 g of product (I), with a yield of 93.4% and an HPLC purity of ≥99.3%.
Embodiment 3
[0042] Preparation of N-acetyl-β-alanine (I)
[0043] In a 1000mL reaction flask, add 360mL toluene, 120g β-alanine (1.348mol), 111.2g acetyl chloride (1.417mol), heat up to 50°C, react for 5 hours, sample ninhydrin does not develop color, cool down to -3 °C, stirred for 1 hour, filtered with suction to obtain a solid, and dried to obtain 169.0 g of product (I), with a yield of 95.7% and an HPLC purity of ≥99.3%.
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Abstract
The invention discloses a preparing method for N-acetyl-L-carnosine and belongs to the technical field of medical intermediates. The method comprises the steps that beta-alanine is subjected to ammonia acetylization to obtain N-acetyl-beta-alanine; N-acetyl-beta-alanine and L-histidine are condensed to obtain N-acetyl-beta-carnosine. N-acetyl-beta-alanine and an acylation reagent react in a non-polar solvent to obtain N-acetyl-beta-alanyl chloride, and L-histidine and organosilane react under the catalyzing of acid to obtain organosilane-protected L-histidine; then organosilane-protected L-histidine and N-acetyl-beta-alanyl chloride are condensed to obtain organosilane-protected N-acetyl-L carnosine, a polar solvent is added to remove protecting groups, and N-acetyl-L-carnosine is obtained through separation and purification. Or, N-acetyl-beta-alanine and L-histidine are condensed under the action of a condensing agent to obatin N-acetyl-L-carnosine.
Description
technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of N-acetyl-L-carnosine. Background technique [0002] The English name of N-acetyl-L-carnosine is N-Acetyl-L-Carnosine, and the chemical name is N-acetyl-β-alanyl-L-histidine (N-Acetyl-β-Alanyl-L-Histidine) , is a white crystalline powder with the following structural formula: [0003] [0004] In 1991, Dr. Babizizhayev of Russia and Dr. Edoardo Bozzo Costa of Italy and Mr. OvidioCaveriof Bruschettini S.r.l., Genoa began a cooperative research to explore the use of N-acetyl-L-carnosine as an ophthalmic drug. They have excellently proved that N-acetyl-L-carnosine is useful for treating the elderly It is very effective for cataract diseases, and the clinical application results have also promoted the commercial development of N-acetyl-L-carnosine. Many companies have begun to produce and sell N-acetyl-L-carnosine eye drops...
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