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Novel intermediate for sweetener with high sweetness and process for producing the same

a sweetener and high sweetness technology, applied in the field of 3substitutedphenyl3merthylbutyric acid and 3substitutedphenyl3methylaldehyde derivatives, can solve the problems of unstable aspartame and unsatisfactory reaction

Inactive Publication Date: 2005-01-20
AJINOMOTO CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present inventors have studied earnestly to solve the above problem, and as a result succeeded in newly synthesizing a 3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl aldehyde and found that the compound is extremely useful as an intermediate for the production of the N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester. Further, the inventors have discovered an efficient process for producing the compound, which is shown in the following reaction process 2.

Problems solved by technology

In recent years, as eating habits have changed dramatically, excessive weight gain caused by the increasing amounts of sugar found in foods have resulted in health related problems.
However, aspartame is somewhat unstable.
Therefore, from the point of industrial profitability, such a reaction is not desirable.

Method used

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  • Novel intermediate for sweetener with high sweetness and process for producing the same
  • Novel intermediate for sweetener with high sweetness and process for producing the same
  • Novel intermediate for sweetener with high sweetness and process for producing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 3-(3-methanesulfonyloxy-4-methoxyphenyl)-3-methylbutyric acid

To sodium hydroxide in the pellet form (70.8 g), toluene (200 ml) and distilled water (350 ml) were added to dissolve completely the solid material. Subsequently, 2-methoxy phenol (200 g) was added dropwise thereto over a period of 30 minutes, and then methanesulfonyl chloride (184.4 g) was added dropwise thereto at room temperature over a period of 1 hour, and thus obtained mixture as it is, was stirred for 10 hours. Subsequently, the organic layer was separated, and the obtained solution as it is, was subjected to a step for removal of the solvent by distillation under reduced pressure. Thus obtained residue was subjected a step for distillation under reduced pressure of 1.1 to 1.4 mmHg (146.7 to 186.7 Pa), to obtain unreacted 2-methoxy phenol (64 g) and 2-methanesulfonyloxy anisole (223.6 g, yield: 68%).

A mixture of 2-methanesulfonyloxy anisole (4.0 g) and 3-methylcrotonic acid (1.0 g) was stirred, and ...

example 2

Synthesis of 3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyric acid

A mixture of 2-methanesulfonyloxy anisole (240 g) and 3-methylcrotonic acid (39 g) was stirred, and to the thus mixed solution, aluminum chloride (104 g) was added, and the mixture was stirred for 5 hours at 70° C., and then further stirred for 2 hours at 100° C. The obtained solution was cooled to about room temperature, and then 6N hydrochloric acid (HCl) solution (390 ml) was added thereto, and the mixture was stirred for 3 hours vigorously. The solution obtained was extracted with the use of methylene chloride (300 ml), and the organic layer separated was further extracted with the use of two normal (2N) sodium hydroxide (NaOH) aqueous solution (400 ml). Subsequently, 6N hydrochloric acid (HCl) solution was further added to the aqueous layer separated, to acidify the solution. The obtained aqueous solution was extracted with methylene chloride (300 ml) twice, and thereafter, thus obtained organic layer was concentr...

example 3

Synthesis of 3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl aldehyde

Into a chemical reactor for hydrogen addition (hydrogenation) under elevated pressure, 3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyric acid (13.6 g), pivalic acid anhydride (22.8 g) and acetone (100 ml) were filled, and thereafter the mixture was bubbled with nitrogen gas for 30 minutes to substitute nitrogen gas completely for the gas in the system of reaction, whereby the system was filled with nitrogen gas. Palladium acetate (137 mg) and tetrahydrofuran solution (5 ml) of tri(p-tolyl) phosphine (930 mg) prepared previously, were added thereto, and then the mixture was stirred under hydrogen pressure of 5 MPa at 80° C. for 24 hours. From the obtained reaction solution, acetone was removed by vaporization. The remaining residue was subjected to a purification process with the use of a column chromatography to obtain 3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl aldehyde (10.2 g, yield: 80%).

1H NMR (CDCl3):

δ:1.41 (s, 6...

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Abstract

The present invention relates to a 3-substituted-phenyl-3-merthylbutyric acid and 3-substituted-phenyl-3-merthylaldehyde derivatives, which are useful in the production of N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester, which is a sweetener with high sweetening potency.

Description

FIELD OF THE INVENTION The present invention relates to a 3-substituted-phenyl-3-merthylbutyric acid and 3-substituted-phenyl-3-methylaldehyde derivatives, which are useful in the production of N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester, which is a sweetener with high sweetening potency. BACKGROUND OF THE INVENTION In recent years, as eating habits have changed dramatically, excessive weight gain caused by the increasing amounts of sugar found in foods have resulted in health related problems. Accordingly, the development of a low-calorie sweetener (sweetening agent) that replaces sugar has been strongly in demand. An example of such a low-calorie sweetener that is commonly used is aspartame, which is safe and effective for providing a high level of sweetness. However, aspartame is somewhat unstable. To solve these problems, an —[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester shown ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C45/41C07C47/277C07C51/367C07C303/30C07C309/66C07K5/072C07K5/075
CPCC07C45/41C07C47/277C07C51/367C07C303/30C07K5/06113C07C59/64C07C309/66
Inventor KAWAHARA, SHIGERUMORI, KENICHINAGASHIMA, KAZUTAKATAKEMOTO, TADASHI
Owner AJINOMOTO CO INC
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