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A kind of preparation method of optically active 3-aminobutanol and 3-aminobutyric acid

A technology of alkyl and chiral carbon, which is applied in the preparation of amino hydroxyl compounds, chemical instruments and methods, and the preparation of organic compounds, etc., which can solve the problems of high toxicity of raw materials, low yield, and many waste materials

Active Publication Date: 2017-04-12
JIANGXI LONGLIFE BIO PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0041] The technical problem to be solved by the present invention is to overcome the preparation method of optically active 3-aminobutanol in the prior art with expensive raw materials, inflammable and explosive raw materials, high toxicity of raw materials, too high cost, low purity and low yield. Low, more waste materials are easy to cause waste of raw materials and disadvantages such as industrial production, and a preparation method for optically active 3-aminobutanol and 3-aminobutyric acid is provided

Method used

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  • A kind of preparation method of optically active 3-aminobutanol and 3-aminobutyric acid
  • A kind of preparation method of optically active 3-aminobutanol and 3-aminobutyric acid
  • A kind of preparation method of optically active 3-aminobutanol and 3-aminobutyric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Embodiment 1: the synthesis of ethyl 3-acetamidocrotonate (p-toluenesulfonic acid catalysis)

[0105] Add 52 kilograms of ethyl acetoacetate, 35 kilograms of acetamide and 300L cyclohexane in a 500-liter reactor, and stir thoroughly. Then add 3 kilograms of p-toluenesulfonic acid, and slowly heat up to reflux and divide water through the water separator. When the reaction was about 24 hours, the sample was detected by GC, and when the ratio of product and raw material reached 9:1, the stirring was stopped and left to stand. Separate the layers while hot, cool the upper layer to room temperature, then add 50 kg of water to wash and separate the layers, concentrate the upper organic layer until a large amount of solid precipitates, filter to obtain white crystals, and vacuum dry to obtain 37.6 kg of white solids, with a yield of 55%. Melting point: 64-65°C. Gas phase detection purity: 98.7%.

[0106] 1 H NMR (300MHz, CDCl3): δ1.28(t, J=7.2Hz, 3H), 2.14(s, 3H), 2.38(s,...

Embodiment 2

[0107] Embodiment 2: Synthesis of ethyl 3-acetamidocrotonate (catalyzed by boron trifluoride ether)

[0108] Add 500 grams of ethyl acetoacetate, 340 grams of acetamide and 3 liters of cyclohexane into a 5-liter round bottom flask, and stir well. Then add 25 grams of boron trifluoride diethyl ether, and slowly heat up to reflux and separate water through a water separator. When the reaction was about 24 hours, the sample was detected by GC, and when the ratio of product and raw material reached 9:1, the stirring was stopped and left to stand. The layers were separated while hot, the upper layer was cooled to room temperature, and then 500 ml of water was added to wash the layers. The upper organic layer was concentrated until a large amount of solids were precipitated. The white crystals were obtained by filtration and vacuum-dried to obtain 394 g of white solids, with a yield of 61%. Melting point: 64.5-65°C. Gas phase detection purity: 99.1%.

[0109] 1 H NMR (300MHz, CD...

Embodiment 3

[0110] Embodiment 3: the synthesis of (R)-3-acetylaminobutyric acid ethyl ester

[0111] Add 200 grams of ethyl 3-acetylaminocrotonate and 800 milliliters of methanol into a 2L hydrogenation reactor, and replace with nitrogen for 30 minutes; then 83 milligrams of Rh(SSRR-TangPhos)(COD)BF 4 Add to the reaction kettle. Carefully add hydrogen, and maintain 1-5 atmospheric pressure at room temperature for 20-24 hours; the reaction of the raw materials was detected by gas chromatography, and the discharge was concentrated to obtain 186 grams of oil, with a yield of 92%, ee99.4%. ee Gas phase detection conditions: Astec CHIRALDEXTM B-DM30mx0.32mmx0.12um chromatographic column. Carrier gas: nitrogen; flow rate: 1.5mL / min; column temperature: 110°C constant temperature; retention time: R‐3‐acetylaminobutyrate 14.7 minutes, S-3‐acetylaminobutyrate 12.8 minutes.

[0112] 1 H NMR (300MHz, CDCl 3 ):δ6.15(brs,1H),4.39-4.31(m,1H),4.21(q,7.2Hz,2H),2.52(dd,2.8,5.3Hz,2H),1.96(s,3H),1.27 (...

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Abstract

The present invention discloses a preparation method for optical activity active 3-amino butanol and optical activity 3-amino butyric acid. The optical activity active 3-amino butanol preparation method comprises: in a solvent, under effects of a hydroboration reduction agent and a Lewis acid, carrying out a reduction reaction on a compound represented by a formlu 65 to produce a compound represented by a formlu 14. The optical activity active 3-amino butyric acid preparation method comprises: carrying out a hydrolysis reaction on a compound represented by a formlu 64 to produce a compound represented by a formlu 65. According to the present invention, the preparation method has characteristics of cheap and easily-available raw materials, simple operation, short process route, no hazard of raw materials, high yield, little waste production, environment protection, high raw material conversion rate, high product chemical purity and high product optical purity, and the industrialization is easily achieved. The formulas 64, 65 and 14 are defined in the instruction.

Description

technical field [0001] The invention specifically relates to a preparation method of optically active 3-aminobutanol and 3-aminobutyric acid. Background technique [0002] Dolutegravir, Dolutegravir, is developed by GlaxoSmithKline and recently approved by the FDA as an anti-HIV drug, see structural formula 1, and its trade name is Tivicay. FDA officials said that HIV-infected people need targeted treatment based on individual conditions, and acknowledged the breakthrough of Tivicay, which provides new options for patients. [0003] [0004] In a study conducted in 2011 and 2012, after 48 and 96 weeks of Tivicay treatment, 88% of patients showed significant improvement, which was better than Gilead's Atripla. So in February 2013, the FDA announced that it would expedite the review of Tivicay and approve it on August 13, 2013. Subsequently, the Canadian health department also approved dolutegravir on November 4, 2013. [0005] Tivicay is produced by GlaxoSmithKline and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C215/08C07C227/30C07C229/08
Inventor 吴生文田重威胡四明白君林李天桥吴磊李文革
Owner JIANGXI LONGLIFE BIO PHARM CO LTD
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