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Method for preparing L-serine-**N

A technology of serine and -15N is applied in the field of preparation of L-serine-15N to achieve the effect of high utilization rate

Inactive Publication Date: 2008-02-27
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Above synthetic method, there is no comparatively suitable preparation L-serine- 15 N approach, need to explore new L-serine- 15 The synthesis route of N, and improve the synthesis process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 0.3mol Na 15 NO 2(Abundance is 99.3%), 0.3mol of diethyl malonate, 80ml of toluene and 10g of water are added to a 500ml three-necked flask and stirred evenly, the temperature of the reaction system is reduced to 5℃, and 1mol is added dropwise within 1 hour Acetic acid; the temperature was raised to 30°C and stirring was continued for 10 hours. After the reaction, toluene and water were added, and diethyl malonate containing oximino was obtained through extraction and separation. 15 The toluene phase of N is washed, dried and distilled under reduced pressure to remove the toluene to obtain diethyl oximinomalonate- 15 N.

[0025] Synthesize 0.2mol of diethyl oxime malonate- 15 N, 0.4mol acetic acid, 0.8mol acetic anhydride, and 2g 5% Pd / C catalyst were added to a 500ml pressure-resistant reactor and stirred uniformly, replaced with nitrogen and hydrogen 10 times respectively, and controlled the reaction temperature to 40°C and pressure to 0.1MPa , Continue to pass hydrogen t...

Embodiment 2

[0029] 1mol Na 15 NO 2 (Abundance is 99.3%), 0.3mol of diethyl malonate, 40ml of toluene and 4g of water are added to a 500ml three-necked flask and stirred evenly, the temperature of the reaction system is reduced to 5℃, and 5mol is added dropwise within 2 hours Acetic acid; the temperature was raised to 30°C and stirring was continued for 10 hours. After the reaction, toluene and water were added, and diethyl malonate containing oximino was obtained through extraction and separation. 15 The toluene phase of N is washed, dried and distilled under reduced pressure to remove the toluene to obtain diethyl oximinomalonate- 15 N.

[0030] Synthesize 0.2mol of diethyl oxime malonate- 15 N, 2mol acetic acid, 1.2mol acetic anhydride and 8g 5% Pd / C catalyst were added to a 500ml pressure-resistant reactor and stirred uniformly, replaced with nitrogen and hydrogen 10 times respectively, and controlled the reaction temperature to 70°C and pressure to 1.0MPa. Continue to feed hydrogen for 8 ...

Embodiment 3

[0034] 2mol Na 15 NO 2 (Abundance is 99.3%), 0.3mol of diethyl malonate, 100ml of toluene and 20g of water are added to a 500ml three-necked flask and stirred evenly, the temperature of the reaction system is reduced to 5℃, and 2mol is added dropwise within 4 hours Acetic acid; the temperature was raised to 30°C and stirring was continued for 10 hours. After the reaction, toluene and water were added, and diethyl malonate containing oximino was obtained through extraction and separation. 15 The toluene phase of N is washed, dried and distilled under reduced pressure to remove toluene to obtain diethyl oximinomalonate- 15 N.

[0035] Synthesize 0.2mol of diethyl oxime malonate- 15 N, 1 mol acetic acid, 0.4 mol acetic anhydride were added to a 500 ml pressure-resistant reactor and stirred uniformly, and excess zinc powder was added in batches for reduction reaction. The reaction temperature was controlled to 80° C., the pressure was normal pressure, and the reaction was carried out ...

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PUM

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Abstract

The invention discloses a making method of L-serine-15N, which comprises the following steps: adopting Na15NO2 and diethyl malonate as raw material to synthesize acetamino-diethyl malonate-15N; using the obtained acetamino-diethyl malonate-15N to synthesize N-acetyl-DL-serine-15N; detaching through enzyme method to obtain the product with optical purity over 98. 5% and chemical purity over 98%. The invention improves the utility of raw material of 15N, which makes the abundance of 15N in the product over 98%.

Description

Technical field [0001] The invention relates to a method for preparing organic compounds labeled with stable isotopes, in particular to a kind of L-serine- 15 Preparation method of N. Background technique [0002] Nitrogen-15 (abbreviated 15 N, the same below) is a stable isotope of nitrogen, 15 N markers can be used as tracers and are widely used in biochemistry, medicine, pharmacology, agricultural sciences and other fields, especially for life science research. Serine- 15 N can be used as a tracer to study metabolism in organisms. Add L-serine to food- 15 N injection can be used to study the metabolic pathway of serine in animals (Shemin, D., J. Biol. Chem., 1945, 158: 297; Elwyn, D., Sprinson, DB, J. Biol. Chem., 1949, 178 :475), to study the relationship between L-serine metabolism and protein synthesis rate in human body (Monica, C., David, H., Rapid Commun. Mass. Spectrum., 1995, 9(8): 655-659; Stein, TP , Settle, RG, Albina, JA, Denpsey, DT, Melnick, G., J. Natr. 1986, 11...

Claims

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Application Information

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IPC IPC(8): C07C229/22C07C227/00C07B59/00
Inventor 杨飞卢伟京杜晓宁徐建飞
Owner SHANGHAI RES INST OF CHEM IND
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