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Preparation and purification method for heterocyclic compounds

A purification method and compound technology, applied in the direction of chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of harsh use conditions, low product purity, and less than product purity, and achieve mild reaction conditions and process Simple operation and high product purity

Pending Publication Date: 2019-09-27
2Y CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, after the literature is freeze-dried, the product purity obtained is less than 50% (HPLC), and any purification method is not described in this patent, and the product purity obtained cannot be further improved
In addition, the patented method needs to use harsh freeze-drying conditions, and the production cost is expensive
In summary, the method described in this patent cannot react completely, there is no purification method, the product purity is low, and the cost of freeze-drying method is high, so it is not suitable for commercial production

Method used

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  • Preparation and purification method for heterocyclic compounds
  • Preparation and purification method for heterocyclic compounds
  • Preparation and purification method for heterocyclic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1. Preparation and purification of nicotinamide ribosinium chloride crude product

[0049]

[0050] Dissolve 50g of compound B in 500mL of isopropanol, then add 10g of ammonium chloride, 1g of 5% palladium carbon (wet product, water content about 50%), feed air, control the pressure to about 0.2MPa, and stir at 20°C The reaction, about 20 hours, was monitored until the reaction was complete. Remove palladium carbon by filtration, decolorize the filtrate with activated carbon, concentrate under reduced pressure, add 500mL of ethanol to the obtained crude product, stir and crystallize, filter with suction, and dry the filter cake to obtain 50g of nicotinamide riboside inium chloride solid, the yield is 89%, the purity 99.4%.

[0051] 1 H-NMR (D 2 O,400MHz),9.46(s,1H),9.12(m,1H),8.83(m,1H),8.13(m,1H),6.11(d,1H),4.37(t,1H),4.21(m , 1H), 4.10 (m, 1H), 3.92 (m, 1H), 3.75 (m, 1H), mass spectrum m / z (ESI): 255.

Embodiment 2

[0052] Example 2. Preparation and purification of nicotinamide ribosinium chloride salt

[0053] Dissolve 10g of compound B in 200mL of water, then add 2g of ammonium chloride, 1g of 5% platinum carbon (wet product, water content about 50%), feed air, pressure about 2.0MPa, stir at 40°C, monitor until the reaction is complete , about 20 hours. Remove the catalyst by filtration, add activated carbon to the filtrate for decolorization, concentrate under reduced pressure, add 100 mL of isopropanol to the obtained crude product, stir and crystallize, filter with suction, and dry the filter cake to obtain 8.9 g of nicotinamide riboside inium chloride solid, with a yield of 79% , 99.2% purity.

[0054] 1 H-NMR (D 2 O,400MHz),9.46(s,1H),9.12(m,1H),8.83(m,1H),8.13(m,1H),6.11(d,1H),4.37(t,1H),4.21(m , 1H), 4.10 (m, 1H), 3.92 (m, 1H), 3.75 (m, 1H), mass spectrum m / z (ESI): 255.

Embodiment 3

[0055] Example 3. Preparation and purification of nicotinamide ribosinium chloride salt

[0056] Dissolve 10g of compound B in 200mL of methanol, then add 2g of ammonium chloride, 1g of 5% platinum carbon (wet product, water content about 50%), blow in air to about 1.0MPa, stir at 30°C, and monitor until the reaction Complete, about 20 hours. Filtrate, concentrate the filtrate under reduced pressure, add 100 mL of ethanol to the obtained crude product, stir and crystallize, filter with suction, and dry the filter cake to obtain 9.2 g of nicotinamide riboside inium chloride solid, with a yield of 82% and a purity of 98.5%.

[0057] 1 H-NMR (D 2 O,400MHz),9.46(s,1H),9.12(m,1H),8.83(m,1H),8.13(m,1H),6.11(d,1H),4.37(t,1H),4.21(m , 1H), 4.10 (m, 1H), 3.92 (m, 1H), 3.75 (m, 1H), mass spectrum m / z (ESI): 255.

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Abstract

The invention relates to synthesis of heterocyclic compounds and in particular relates to a preparation and purification method for nicotinamide nucleoside onium salts. The method comprises the following steps: dissolving a compound B and an ammonium salt into a solvent 1 in the presence of a catalyst, introducing air to react in a closed manner at a suitable temperature, removing the catalyst by filtration after the reaction is ended, and concentrating reaction liquid so as to obtain a crude product; dissolving the crude product in a solvent 2, separating out a crystal, and performing filtering and drying, thereby obtaining the nicotinamide nucleoside onium salts shown as a formula (I). The preparation and purification method disclosed by the invention is simple in process operation, high in reaction speed, high in product purity, recyclable in catalyst, low in cost and environmentally friendly, is suitable for commercialized production, and has excellent application prospects.

Description

technical field [0001] The invention relates to the synthesis of heterocyclic compounds, in particular to the preparation and purification method of nicotinamide ribosinium salt. Background technique [0002] Nicotinamide Riboside Chloride (see formula I for structure) has great potential as a natural and nutritional supplement. Among them, Nicotinamide Riboside Chloride, English name Nicotinamide Riboside Chloride, referred to as NR, CAS registration number 23111-00- 4. Nicotinamide adenine dinucleotide (nicotinamide adenine dinucleotide, NAD + ) pyridine-nucleoside precursor. NR was discovered in the 1940s. At that time, it was discovered that the growth factor (factorV) that promoted the growth of Haemophilus influenzae purified from blood had three forms: nicotinamide adenine dinucleotide (NAD) + ), nicotinamide mononucleotide (NMN) and nicotinamide ribosinium chloride (NR). And NR is the substance that makes the bacteria grow the fastest (Gingrich, W. "Codehydrogena...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/048C07H1/00C07H1/06
CPCC07H19/048C07H1/00C07H1/06Y02P20/584
Inventor 王元刘传军何训贵
Owner 2Y CHEM