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New synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid

A technology of enantiomers and benzyloxy, which is applied in the field of synthesis of chiral compounds, can solve problems such as no synthetic research, and achieve the effect of convenient scientific research

Inactive Publication Date: 2016-06-15
JIANGXI SCI & TECH NORMAL UNIV
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Problems solved by technology

[0002] New compound fragments (R)-4-(4-(benzyloxy)phenyl)-2-hydroxybutanoic acid and (S)-4-(4-(benzyloxy)phenyl)-2-benzyl Hydroxybutyric acid is an intermediate of many drug molecules, but no synthetic research has been done on it in the world

Method used

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  • New synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid
  • New synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid

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Embodiment 1

[0031] The synthetic method of (S)-4-(4-(benzyloxy) phenyl)-2-benzyl hydroxybutyric acid specifically comprises the steps:

[0032] 1) Synthesis of compound 3

[0033] Dissolve p-hydroxybenzaldehyde (10.0g, 81.88mmol) in acetonitrile (300mL), cool to zero, add potassium carbonate (16.98g, 122.83mmol), stir for ten minutes, add benzyl bromide (9.92mL, 83.52mmol) and Tetrabutylammonium iodide (3.0 g, 8.19 mmol), raised to room temperature, stirred overnight. After the reaction was complete, a saturated solution of ammonium chloride was added to quench the reaction. Extracted with ethyl acetate (300 mL), the organic phase was washed with saturated brine (50 mL), dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation to obtain compound 3.

[0034] 2) Synthesis of Compound 4

[0035] Compound 3 was dissolved in methanol (200 mL), cooled to zero degree, sodium borohydride (6.05 g, 160 mmol) was slowly added, and kept stirring at zero degree...

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Abstract

The invention discloses a new synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid. The invention adopts cheap and easily available p-hydroxy benzaldehyde and (R)-(+)-2, 2-dimethyl-1, 3-dioxolane-4-formaldehyde as initial raw materials to conduct total synthesis study on brand new compounds (R)-4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid and (S)-4-(4-(benzyloxy)phenyl)-2-benzyl hydroxybutyric acid. The invention uses an asymmetric synthesis method to synthesize two molecules by one route, fills the blank, and provides convenience for future scientific research.

Description

technical field [0001] The invention relates to a synthesis method of chiral compounds, in particular to a new synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid. Background technique [0002] New compound fragments (R)-4-(4-(benzyloxy)phenyl)-2-hydroxybutanoic acid and (S)-4-(4-(benzyloxy)phenyl)-2-benzyl Hydroxybutyric acid is an intermediate of many drug molecules, but no synthetic research has been done on it in the world. At present, the only molecules similar to it in the world are the products of racemization at the chiral center. Contents of the invention [0003] The purpose of the present invention will overcome the deficiencies in the prior art exactly, provide a kind of new synthetic method of two kinds of enantiomers of 4-(4-(benzyloxy) phenyl)-2-hydroxybutyric acid , p-(R)-4-(4-(benzyloxy)phenyl)-2-hydroxybutanoic acid and (S)-4-(4-(benzyloxy)phenyl)-2-benzyl Hydroxybutyric acid was synthesized with the aim of solving the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/66
CPCY02P20/55C07C51/09C07C67/31C07C67/317C07C201/12C07C59/66C07C69/734C07C205/57
Inventor 王晓季冯俊敏黄双平冷晓张志滨林爽杰杨申坤粱程徐天祥
Owner JIANGXI SCI & TECH NORMAL UNIV
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