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A kind of synthetic method of selenomethylselenocysteine
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A technology of methylselenocysteine and selenocysteine, which is applied in the direction of organic chemistry and the like, can solve the problems of complex process route, high raw material price and high production cost, and achieves easy availability of raw materials and low cost of raw materials. , the effect of moderate reaction temperature and time
Inactive Publication Date: 2020-04-07
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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4. Synthesis of α-aminoacrylic acid derivatives, etc., but these synthesis methods have defects such as high raw material prices leading to high production costs, complicated process routes, and large environmental pollution
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Embodiment 1
[0022] (1) In a 100mL three-neck flask with a rotor and a thermometer, add 3.74g (about 20mmol) of 2-methyl-4-benzylidene-5-oxazolinone and 60mL of 1,4-dioxane, and Under argon protection, after stirring for 10 minutes, start to add 3.76g (about 20mmol) dimethyl diselenide and 84.6mg (about 0.2mmol) silver tris(2-pyrrolyl)phosphine tetrafluoroborate, and control the reaction temperature to 75-80°C , After the addition, the reaction was stirred at constant temperature for 10h. After the reaction was completed, it was concentrated by rotary evaporation, and then purified by column chromatography to obtain 3.62 g of a brownish-yellow oil, with a yield of about 88.2%. MS(FAB):m / z 205(M + ); 1 H NMR (DMSO-d 6 )δ: 0.95(s,6H), 6.31(s,1H). 13 C NMR (DMSO-d 6 )δ: 9.1, 18.1, 123.9, 142.7, 168.3.
[0023] (2) Compound (III) (10mmol) and catalyst tris(2-pyrrolyl) rhodium chloride (0.1mmol) are added in the hydrogenation reactor, and the system is repeatedly vacuumized and filled wit...
Embodiment 2
[0026] (1) In a 100mL three-neck flask with a rotor and a thermometer, add 3.74g (about 20mmol) of 2-methyl-4-benzylidene 5-oxazolinone and 60mL of 1,4-dioxane, and Under argon protection, after stirring for 10 minutes, start to add 3.76g (about 20mmol) dimethyl diselenide and 91mg (about 0.2mmol) tris(2-pyridyl)phosphine rhodium tetrafluoroborate, control the reaction temperature at 75-80°C, add After completion, the reaction was stirred at constant temperature for 8h. After the reaction was completed, it was concentrated by rotary evaporation, and then purified by column chromatography to obtain 3.74 g of a brownish-yellow oil, with a yield of about 91.2%. MS(FAB):m / z 205(M + ); 1 H NMR (DMSO-d 6 )δ: 0.95(s,6H), 6.31(s,1H). 13 C NMR (DMSO-d 6 )δ: 9.1, 18.1, 123.9, 142.7, 168.3.
[0027] (2) Add compound (III) (10mmol) and catalyst hydrogenation tris(2-pyridyl) iridium (0.1mmol) into the hydrogenation reaction kettle, and inject the newly distilled THF 10mL after the sy...
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Abstract
The invention discloses a synthetic method for Se-methylselenocysteine, and belongs to the field of fine chemical or organic synthesis. The method comprises the following steps: performing a catalyticreaction by using 2-methyl-4-benzylidene-5-oxazolidinone (I) shown in the description and dimethyldiselenide (II) shown in the description as raw materials to obtain a compound (III), performing catalytic hydrogenation to obtain a compound (IV), finally performing hydrolysis, and adjusting a pH to obtain the target compound (V) shown in the description. The method disclosed by the invention has the advantages that the raw materials are cheap and easy to obtain, the preparation process conditions are mild and controllable, the reaction temperature and time are moderate, the utilization rate ofthe raw materials is higher, and the total yield is high, wherein the total yield reaches 65% or more.
Description
technical field [0001] The invention relates to the synthesis of selenium-containing amino acid compounds, in particular to the synthesis of selenomethylselenocysteine, belonging to the field of organic synthesis. Background technique [0002] Selenium methyl selenocysteine, English name Se-methylselenocysteine, molecular formula C 4 h 9 NO 2 Se, its structural formula is as shown in (V): [0003] [0004] Selenomethylselenocysteine is a class of selenium-containing amino acid compounds, and is an intermediate of many fine chemicals, used in pesticides, medicines and other fields. L-selenium-methylselenocysteine is a new type of organic selenium compound. It is a small molecule organic selenium variety with clear structure and stable content. It belongs to the third generation of selenium supplement products. It has strong biological activity and high utilization rate , is also one of the best selenium supplements so far, and can be widely used in the fields of fo...
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