Method for producing alpha -mino-gamma-butyrolactone

A manufacturing method, technology of butyrolactone, applied in organic chemistry methods, chemical instruments and methods, asymmetric synthesis, etc., can solve unsatisfactory industrial production methods and other problems

Inactive Publication Date: 2013-09-04
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, if this method is used, the yield is 58...

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  • Method for producing alpha -mino-gamma-butyrolactone
  • Method for producing alpha -mino-gamma-butyrolactone
  • Method for producing alpha -mino-gamma-butyrolactone

Examples

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Embodiment 1

[0028] Example 1 (production of α-amino-γ-butyrolactone hydrochloride)

[0029]

[0030] While stirring the mixture of L-methionine (100.0g, 0.67mol) and water (200ml), after heating up to 81°C, add monochloroacetic acid (63.3g, 0.67mol) dropwise in water ( 100ml) solution. The reaction mixture was further stirred at this temperature for about 3 hours. After cooling the reaction mixture to 25° C., it was washed with ethyl acetate (200 ml×2 times, 100 ml×3 times) to obtain an aqueous layer (about 393 g). Among them, 79.9g of the water layer (equivalent to methionine 0.13mol) was used, concentrated to a residual amount of about 29g under the condition of 50-60°C / about 5KPa, and 35% hydrochloric acid (14.0g, 0.13mol), stirred for about 0.5 hours. After cooling to 25°C, 2-propanol (100ml) was added dropwise, followed by further cooling to 0-5°C. Filtration, washing with 40 ml of 2-propanol, and drying under reduced pressure gave 12.6 g of α-amino-γ-butyrolactone hydrochlori...

Embodiment 2

[0031] Example 2 (production of α-amino-γ-butyrolactone hydrochloride)

[0032] While stirring the mixture of L-methionine (200g, 1.34mol) and water (266ml), while raising the temperature to 85°C, add monochloroacetic acid (127g, 1.34mol) dropwise in water (200ml) at 85-100°C for 2 hours solution. The reaction mixture was further stirred at 85-95°C for about 3 hours. After cooling the reaction mixture to 25° C., it was washed with ethyl acetate (400 ml×1 time, 200 ml×2 times) to obtain a water layer (about 665 g). Among them, 453 g of the aqueous layer (equivalent to methionine 136 g, 0.91 mol) was used, concentrated to a residual amount of about 251 g under the condition of about 55 ° C / about 5 KPa, and hydrogen chloride was dissolved in about 5 hours while stirring at about 50 ° C. Gas (110 g, 3.02 mol) was bubbled into the concentrate. After cooling to 5-10° C., the solid was filtered and washed with 2-propanol (140 ml). Drying under reduced pressure gave 95.2 g of α-...

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Abstract

A method for producing alpha -mino-gamma -butyrolactone or a salt thereof, which comprises a step wherein methionine and a haloacetic acid, namely chloroacetic acid or bromoacetic acid, are caused to react with each other in a solvent, and which is characterized in that the solvent contains 60% by weight or more of water relative to the total weight of the solvent. By this method, a-amino-?-butyrolactone or a salt thereof can be produced with high yield.

Description

technical field [0001] The present invention relates to an industrial production method of α-amino-γ-butyrolactone. Background technique [0002] α-Amino-γ-butyrolactone is useful as an intermediate for the production of pharmaceuticals and pesticides. For example, Schemes 69 and 70 of US2010 / 0189687 describe the use of α-amino-γ-butyrolactone as an intermediate of cytochrome P450 monooxygenase inhibitors. [0003] In addition, Tetrahedron Letters, Vol.50, p.5067-5070, (2009) and its supporting materials describe a method for producing α-amino-γ-butyrolactone hydrochloride by reacting methionine with chloroacetic acid . Specifically, methionine and chloroacetic acid were reacted in a mixed solvent of water, 2-propanol, and acetic acid (the volume ratio of each was 10:10:4 / converted weight ratio was about 10:8:4), the solvent was distilled off, and blown Hydrogen chloride gas is injected to carry out crystallization to produce α-amino-γ-butyrolactone hydrochloride. Howeve...

Claims

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Application Information

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IPC IPC(8): C07D307/33C07B53/00
CPCC07B53/00C07D307/33
Inventor 王维奇
Owner SUMITOMO CHEM CO LTD
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