Kanegafuchi Kagaku Kogyo Kabushiki Kaisha

Kaneka Corporation

Kanegafuchi Chemical Industry Co., Ltd.

Kazunori Kan

Kiyoshi Watanabe

Takehisa Ohashi

Noboru Ueyama

Isao Sada

Kenji Inoue

Natsuki Mori

Akimasa Miyama

Tadashi Sugawa

Masami Shimazaki

Fumihiko Kanou

Toshihiro Takeda

Naoaki Taoka

Tadashi Moroshima

Nobuo Nagashima

Shingo Matsumoto

Noritaka Yoshida

Hideo Kondo

Kenji Nomura

Mizuho Honda

Takeshi Furuta

Hiroshi Murakami

Takeisa Ohashi

Process for preparing optically active alcoholic compounds

Process for the reduction of carbonyl compounds

Process for preparing pyrrolidine derivatives

Process for preparing carboxylic acid derivative

Process for producing optically active 2-alkoxycyclohexanol derivatives

Process for preparing an enol silyl ether compound

The present invention relates to .beta.-lactam compound having the formula (I): ##STR1## wherein R.sup.1 is a trialkylsilyl group, dimethyl-1,1,2-trimethylpropylsilyl group, acetyl group, benzyloxycarbonyl group, O-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group or t-butyl group, R.sup.2, R.sup.3 and R.sup.4 are a member selected from the group consisting of a lower alkyl group having 1 to 6 carbon atoms, phenyl group and an aralkyl group and a process for preparing the compound which comprises reacting enolsilylethers having the formula (III): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as above, with chlorosulfonylisocyanate and then reducing the obtained product. The .beta.-lactam compound of the present invention is a useful intermediate for preparing carbapenem .beta.-lactam compound.

Enolsilyl ether compound

A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reactig a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as difined above and R.sup.2, R.sup.3 and R.sup.4 are the same or different and each is a lower alkyl group having 1 to 4 carbon atoms or an aralkyl group, with acetic anhydride in the presence of a base and a catalyst selected from the group consisting of an organic strong acid, a mineral acid, a Lewis acid, a halogenated acyl compound having the formula (IV):

Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives

A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reacting a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2, R.sup.3 and R.sup.4 are a lower alkyl group having 1 to 6 carbon atoms, phenyl group or an aralkyl group, with acetic anhydride in an organic solvent in the presence of a low concentration of a substituted pyridine. According to the present invention, there can be obtained 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives, which are useful intermediates for preparing carbapenem .beta.-lactam antibiotics.

A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reacting a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as defined above, R.sup.2, R.sup.3 and R.sup.4 are a lower alkyl group having 1 to 6 carbon atoms, phenyl group or an aralkyl group and R is a protective group for N, with acetic anhydride in an organic solvent in the presence of a base, and removing the protective group for N. 4-Acetoxy-3-hydroxyethylazetidin-2-one derivatives are useful intermediates for preparing carbapenem .beta.-lactam antibiotics such as thienamycin and penem .alpha.-lactam antibiotics.

Beta-lactam compound and preparation thereof

A process is disclosed wherein an optically active .beta.-mercaptoalkanoic acid represented by formula (I): ##STR1## wherein R.sub.1 is lower alkyl having from 1 to 4 carbon atoms, is prepared by

Process for preparation of an optically active .beta.-mercaptoalkanoic

A process is disclosed wherein an optically active N-mercaptoalkanoylamino acid is prepared by

Process for preparation of optically active N-mercaptoalkanoylamino acids

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Nishinomiya, Japan

Kazunori Kan