Process for producing solid amino acid

Patent metadata

Field	Value
Publication number	US-9302980-B2
Application number	US-201314375975-A
Country	US
Kind code	B2
Filing date	Jan 21, 2013
Priority date	Feb 1, 2012
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

The problem to be solved by the present invention is to easily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, which is useful as a synthetic intermediate for medicines or agrochemicals.
The present invention is characterized in comprising a step of precipitating solid amino acid with high purity. In the present invention, the by-produced salt composed of the sulfonic acid and the amine was removed to the mother liquor by reacting an amine with a sulfonic acid salt of amino acid in an aprotic polar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent.
The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester with a sulfonic acid.

First claim

The invention claimed is:

1. A process for producing an unprotected amino acid comprising 2 to 7 carbon atoms, the process comprising
precipitating a solid of the unprotected amino acid
wherein the precipitating is carried out by adding an amine to a sulfonic acid salt of an unprotected amino acid in an aprotic polar solvent, adding an amine to a sulfonic acid salt of an amino acid produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid in an aprotic polar solvent, adding an amine to a sulfonic acid salt of an amino acid produced by reacting an amino acid tert-butyl ester with a sulfonic acid in an aprotic polar solvent or
by adding a sulfonic acid to an amine salt of an unprotected amino acid in an aprotic polar solvent,
wherein optionally the addition of the amine or the sulfonic acid continues until pH of a solution comprising the sulfonic acid salt or the amine salt reaches a range of isoelectric point of the amino acid pI value ±3.

2. The process according to claim 1 , wherein the aprotic polar solvent is at least one selected from the group consisting of methylene chloride, 1,2-dichloroethane, acetonitrile, acetone, N,N-dimethylformamide, N,N-dimethylacetamide, ethylene glycol dimethyl ether and dimethyl sulfoxide.

3. The process according to claim 1 , wherein:
the sulfonic acid is at least one selected from the group consisting of methanesulfonic acid, p-toluenesulfonic acid, and camphorsulfonic acid; and
the amine is triethylamine.

4. The process according to claim 1 , wherein the amino acid is at least one selected from the group consisting of sarcosine, alanine, 2-amino-2-methylbutanoic acid, tert-leucine, proline, 2-methyl proline, pipecolic acid, nipecotic acid and (1R,2S)-1-amino-2-vinyl-cyclopropanecarboxylic acid.

5. The process according to claim 1 , wherein the process comprises precipitating the solid of the unprotected amino acid by adding the amine to the sulfonic acid salt of the amino acid in the aprotic polar solvent.

6. The process according to claim 1 , wherein the process comprises precipitating the solid of the unprotected amino acid by adding the sulfonic acid to the amine salt of amino acid in the aprotic polar solvent.

Assignees

• Kaneka Corp

Inventors

• Ohnuki Masatoshi
• Nishiyama Akira

Classifications

• C07D207/16

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07C229/32

  the carbon skeleton being unsaturated and containing rings other than six-membered aromatic rings · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title

• C07C2101/02

  Chemistry & Metallurgy · mapped topic

• C07C229/06

  having only one amino and one carboxyl group bound to the carbon skeleton · CPC title