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Preparation method of 3,5,6-substitued caproate derivative

A technology of hexanoate and derivatives, which is applied in the field of preparation of 3,5,6-substituted hexanoate derivatives, can solve the problems of unsuitability for industrialized large-scale production, high requirements on reaction conditions, pollution, etc., and is suitable for large-scale production. Large-scale production, cheap and easy-to-obtain reagents, and environment-friendly effects

Inactive Publication Date: 2016-06-15
ABIOCHEM BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method utilizes sodium cyanide to extend the carbon chain, which has serious environmental pollution, and uses n-butyllithium in the reaction, which requires high reaction conditions, so it is not suitable for industrialized large-scale production.

Method used

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  • Preparation method of 3,5,6-substitued caproate derivative
  • Preparation method of 3,5,6-substitued caproate derivative
  • Preparation method of 3,5,6-substitued caproate derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] a) Dissolve 10 g of the lactone represented by general formula II in 50 mL of absolute ethanol, add 2 drops of concentrated hydrochloric acid, react at room temperature for 2 h, and monitor the completion of the reaction by TLC. The system was adjusted to neutral with sodium bicarbonate, concentrated to remove the solvent, diluted with 100 mL of ethyl acetate, and washed once with 50 mL of saturated brine. Dry over sodium sulfate, concentrate and remove the solvent to obtain 12.1 g of a colorless oil with a yield of 94%, which is directly used in the next reaction.

[0038] b) 10 g of the product of step a) was dissolved in 50 mL of acetone, 7.8 g of sodium iodide was added, and the reaction was refluxed for 48 h, and the reaction was complete as monitored by HPLC. The solid was removed by suction filtration, and the solvent was removed by concentration to obtain 14.0 g of light yellow oil with a yield of 97%, which was directly used in the next reaction.

...

Embodiment 1-1

[0043]

[0044] Dissolve 5 g of the product of step e) (i.e. tert-butyl 2-(6-iodomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetate) in 15 mL of DMSO and add acetic acid Potassium 2.0g, heated to 60°C for 8h. Pour into water, extract with 50mL ethyl acetate, wash with 20mL saturated brine, and dry over sodium sulfate. Concentrate to dryness to obtain 3.8 g, and recrystallize from n-heptane to obtain 3.3 g of white solid, yield 82%.

[0045] The structure of the product was confirmed by H NMR spectroscopy and electrospray ionization mass spectrometry.

[0046] 1 HNMR (300MHz, CDCl 3 ):δ1.40(s,9H),1.41(s,6H),1.48-1.73(dd,2H),2.01(s,3H),2.26-2.51(d,2H),4.09-4.34(d,2H ), 4.43(m,1H), 4.39(m,1H).

[0047] MS (ESI) m / z: (M+H) = 303.1.

Embodiment 1-2

[0049]

[0050] Dissolve 5 g of the product of step e) (i.e. tert-butyl 2-(6-iodomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetate) in 15 mL of DMSO, add cyanide Sodium chloride 0.7g, heated to 50 ℃ for 16h. Pour into water, extract with 50mL ethyl acetate, wash with 20mL saturated brine, and dry over sodium sulfate. Concentrate to dryness to obtain 3.4 g, and recrystallize from n-heptane to obtain 3.1 g of off-white solid. Starting from the lactone represented by the general formula II, the overall yield is 57.9%.

[0051] The structure of the product was confirmed by H NMR spectroscopy and electrospray ionization mass spectrometry.

[0052] 1 HNMR (300MHz, CDCl 3 ):δ1.40(s,9H),1.41(s,6H),1.48-1.73(dd,2H),2.26-2.51(d,2H),2.41-2.66(d,2H),3.8(m,1H ), 4.43(m,1H).

[0053] MS (ESI) m / z: (M+H) = 270.1.

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Abstract

The invention discloses a preparation method of a 3,5,6-substitued caproate derivative which is represented as the general formula (I), wherein the method is prepared with lactone as a raw material and an iodinated substance as an intermediate. The method is low in raw material cost, employs simple reactions, is stable and is high in yield, is easy to control and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a preparation method of 3,5,6-substituted hexanoate derivatives. Background technique [0002] Statins are hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase inhibitors that block intracellular hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase by competitively inhibiting endogenous cholesterol synthesis rate-limiting enzyme (HMG-CoA) reductase The acid metabolism pathway reduces intracellular cholesterol synthesis, thereby feedback stimulating the number and activity of low-density lipoprotein receptors on the surface of cell membranes (mainly liver cells), increasing serum cholesterol clearance and reducing levels. Statins can also inhibit the synthesis of apolipoprotein B-100 in the liver, thereby reducing the synthesis and secretion of triglyceride-rich AV and lipoproteins. Therefore, statins are called "miracle drugs" in reducing blood lipids. [0003] structu...

Claims

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Application Information

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IPC IPC(8): C07D319/06
Inventor 罗煜丁时澄瞿旭东孙传民
Owner ABIOCHEM BIOTECH CO LTD
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