Kaneka Corporation

Kohei Mori

Naoaki Taoka

Akira Nishiyama

Nobuo Nagashima

Daisuke Moriyama

Kenji Inoue

Hirokazu Nanba

Toshihiro Takeda

Satohiro Yanagisawa

Tatsuya Honda

Masashi Izumida

Takahiro Ohishi

Masanobu Sugawara

Masutoshi Nojiri

Narumi Kishimoto

Koji Machida

Takahiro Oishi

A tri-carbobenzoxy-arginine represented by the following formula (2): is produced by carbobenzoxylating the arginine or arginine derivative (1) represented by the following formula (1), or a salt thereof: by adding carbobenzoxy chloride and a base in a water/organic solvent bilayer system to an arginine or arginine derivative (1) represented by the formula (1), or a salt thereof.

Method for producing tri-carbobenzoxy-arginine

The present invention provides a simple industrial process for producing an L- or D-optically active &#x3b1;-methylcysteine derivative or its salt, which is a useful pharmaceutical intermediate, from readily available, inexpensive raw materials. In a process for producing an L- or D-optically active &#x3b1;-methylcysteine derivative or its salt, a racemic N-carbamoyl-&#x3b1;-methylcysteine derivative or its salt is D-selectively cyclized with hydantoinase to produce a D-5-methyl-5-thiomethylhydantoin derivative or its salt and an N-carbamoyl-&#x3b1;-methyl-L-cysteine derivative or its salt, which are then subjected to deprotection of the amino group and the sulfur atom, and hydrolysis.

Process for producing optically active &#x3b1;-methylcysteine derivative

The present invention relates to a method for producing an optically active 3-aminopiperidine or salt thereof. In the method, a racemic nipecotamide is stereoselectively hydrolyzed to obtain an optically active nipecotamide and an optically active nipecotic acid in the presence of an enzyme source derived from an organism, and then the optically active nipecotamide is derived into an optically active aminopiperidine or salt thereof by aroylation, Hofmann rearrangement, deprotection of the amino group and further deprotection; or the optically active nipecotamide is derived into an optically active aminopiperidine or salt thereof by selective protection with BOC, Hofmann rearrangement and further deprotection. It is possible by the present invention to produce an optically active 3-aminopiperidine or salt thereof useful as a pharmaceutical intermediate from an inexpensive and easily available starting material by easy method applicable to industrial manufacturing.

Method for producing optically active 3-aminopiperidine or salt thereof

An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

Process for production of optically active-3-amino-2-hydroxypropionic cyclopropylamide derivatives and salts thereof

The present invention is to provide a process for simply producing an optically active 3-hydroxypropionic ester derivative useful as a medicament intermediate from an inexpensive material. More specifically, the present invention is directed to a process for producing an optically active 3-hydroxypropionic ester derivative comprising reacting an acetic ester derivative available at low cost with a base and a formic ester, thereby converting the acetic ester derivative into a 2-formylacetic ester derivative, and thereafter, stereospecifically reducing the formyl group of the derivative by use of an enzymatic source capable of stereoselectively reducing the formyl group of the derivative.

Process for producing optically active 3-hydroxypropionic ester derivative

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Takasago, Japan

Kohei Mori