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Production method of (r)-3- hydroxy-3-(2-phenylethyl)hexanoic acid and intermediate thereof

A production method, phenylethyl technology, applied in the field of production of (R)-3-hydroxy-3-(2-phenylethyl)hexanoic acid and its intermediates, can solve the problem of high price of bromoacetate question

Inactive Publication Date: 2005-05-18
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bromoacetate is expensive, exhibits strong tearing properties, and reactions to its use have safety and health concerns

Method used

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  • Production method of (r)-3- hydroxy-3-(2-phenylethyl)hexanoic acid and intermediate thereof
  • Production method of (r)-3- hydroxy-3-(2-phenylethyl)hexanoic acid and intermediate thereof
  • Production method of (r)-3- hydroxy-3-(2-phenylethyl)hexanoic acid and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0294] rac ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate

[0295] Magnesium (37.2 g, 1.53 mol) was suspended in THF (60.5 g) and allyl bromide (1.4 g, 0.01 mol) was added in a fine stream. After raising the temperature from 22°C to 38°C, dimethyldichlorosilane (7.3 g, 0.06 mol), 1-phenyl-3-hexanone ( 180.2 g, 1.02 mol), ethyl chloroacetate (139.1 g, 1.13 mol) and allyl bromide (1.4 g, 0.01 mol) in THF (472.9 g). Further ethyl chloroacetate (41.7 g, 0.34 mol) was added in a fine stream at 30-40°C over 1 hour. The mixture was stirred at 40°C for 1.5 hours, and unreacted magnesium was separated by decantation. The decanted reaction mixture was added to a mixture of 35% hydrochloric acid (151.8g, 1.50mol), ammonium chloride (15.9g, 0.30mol) and water (280.7g) with a fine stream, and the layers were separated at 30-40°C . Concentration of the organic layer gave a residue (342.6 g) (quantitative analysis by HPLC) containing the title compound (215.1 g, yield 79.6%).

[0296] 1 ...

Embodiment 2

[0298] rac ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate

[0299] Magnesium (7.45 g, 0.31 mol) was suspended in THF (12.1 g) and allyl bromide (0.28 g, 0.0023 mol) was added in a fine stream. After raising the temperature from 20°C to 30°C, methyltrichlorosilane (3.39 g, 0.023 mol), 1-phenyl-3-hexanone (40.0 g, 0.227 mol), ethyl chloroacetate (27.81 g, 0.23 mol) and allyl bromide (0.275 g, 0.0023 mol) in THF (94.6 g). Further ethyl chloroacetate (8.34 g, 0.07 mol) was added in a fine stream at 30-40°C over 40 minutes.

[0300] The mixture was stirred at 40° C. for 2 hours, and the title compound in the reaction mixture was analyzed to obtain a reaction mixture (46.74 g, yield 77.9%) containing the title compound (quantitative analysis by HPLC). The NMR data is the same as in Example 1.

Embodiment 3

[0302] rac ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate

[0303] Magnesium (7.45 g, 0.31 mol) was suspended in THF (12.1 g) and allyl bromide (0.28 g, 0.0023 mol) was added in a fine stream. After raising the temperature from 20°C to 30°C, silicon tetrachloride (3.86 g, 0.023 mol), 1-phenyl-3-hexanone (40.0 g , 0.227mol), ethyl chloroacetate (27.81g, 0.23mol) and allyl bromide (0.275g, 0.0023mol) in THF (94.6g). Further ethyl chloroacetate (8.34 g, 0.07 mol) was added in a fine stream at 30-40°C over 40 minutes.

[0304] The mixture was stirred at 40° C. for 2 hours, and the title compound in the reaction mixture was analyzed to obtain a reaction mixture (46.76 g, yield 77.9%) containing the title compound (quantitative analysis by HPLC). The NMR data is the same as in Example 1.

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Abstract

A production method of a racemic 3-hydroxy-3-(2-phenylethyl)hexanoic acid ester, which comprises reacting magnesium, haloacetic acid ester and 1-phenyl-3-hexanone.

Description

technical field [0001] The present invention relates to (R)-3-hydroxyl-3-(2-phenylethyl)hexanoic acid which is a useful synthetic intermediate of anti-HIV (AIDS virus) agent and a production method of the intermediate. Background technique [0002] PNU-140690 represented by the following formula (I) is known to be useful as an anti-HIV agent being developed in recent years. As a useful synthetic intermediate of PNU-140690, 3-hydroxy-3-(2-phenylethyl)hexanoic acid represented by the following formula (II) is known. [0003] [0004] The 3-hydroxy-3-(2-phenylethyl)hexanoic acid has an asymmetric carbon atom and includes (R) isomer and (S) isomer, and only the racemic compound (exo rac 3-hydroxy-3-(2-phenylethyl)hexanoic acid). Among these, the (R) isomer of the following formula (III) [(R)-3-hydroxy-3-(2-phenylethyl)hexanoic acid] is preferably used as the above-mentioned synthetic intermediate. [0005] [0006] In terms of the method for the optical resolution of (R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/62C07C45/73C07C45/74C07C49/213C07C51/43C07C51/487C07C69/732C07C211/29C07C217/58
CPCC07B2200/07C07C45/62C07C45/73C07C45/74C07C49/213C07C51/43C07C51/487C07C69/732C07C211/29C07C217/58C07C49/217C07C59/48C07C67/343
Inventor 田中正英松井浩三桂正岩崎光浩前田弘志板谷信重
Owner SUMITOMO CHEM CO LTD
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