Daikin Kogyo Co., Ltd.

Fujisawa Pharmaceutical Company, Ltd.

Central Glass Company, Limited

Takeshi Nakai

Nobuo Ishikawa

Toshiyuki Chiba

Fumiyuki Shirai

Masamichi Maruta

Hiroaki Ohtake

Yoshio Inouye

The invention relates to the preparation of 3,4-disubstituted-2-azetidinone compounds of the formula: ##STR1## in which R.sup.1 is hydrogen or amido-protective group, R.sup.2 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R.sup.3 is lower alkyl, and R.sup.4 is 1-(lower)alkyl-1-hydroxy(C.sub.2 -C.sub.6)alkyl, 1-(lower)alkyl-1-(protected hydroxy)-(C.sub.2 -C.sub.6)alkyl or 2-thioxothiazolidin-3-yl, useful as an intermediate for the production of antimicrobial agents by reacting a compound a compound of the formula: ##STR2## in which R.sup.5 is acyl, or salts thereof, with a compound of the formula:

3,4-disubstituted-2-azetidinone derivatives and processes for

Polyfluoroenolates, R.sup.1 CX.dbd.CR.sup.2 OM (R.sup.1 is F or a perfluoroalkyl group, R.sup.2 is a perfluoroalkyl group, X is F, Cl or Br), are easily formed at good yields by dehydrohalogenation reaction of polyfluoroalcoholates, R.sup.1 CXY--CR.sup.2 HOM (Y is F, Cl or Br), with a strong base such as, e.g., an alkyl metal or an aryl metal. A typical example of the polyfluoroenolates is lithium pentafluoro-2-propenolate which is obtained from hexafluoro-2-propanolate. A polyfluoroenolate of the above general formula can be converted into another polyfluoroenolate having an alkyl or aryl group in place of the halogen X by reaction with an alkyl or aryl metal.

Preparation of polyfluoroenolates

The invention relates to a method of producing an azetidinone derivative of the formula: ##STR1## which comprises reacting a compound of the formula ##STR2## with a compound of the formula ##STR3## and then subjecting the resulting compound to hydrolysis, the substituents above being as defined in the specification.

Azetidinone derivatives and processes for production thereof

An .alpha.-fluoroalkyl carboxylic acid ester of the general formula ##STR1## wherein A is R.sup.1 R.sup.2 COR.sup.3 -- or R.sup.4 CO--, wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl, alkoxyl or phenyl, with or without the formation of a common ring therebetween, R.sup.3 is hydrogen or alkyl, R.sup.4 and R are independently alkyl, and R.sub.f is fluoroalkyl. The .alpha.-fluoroalkyl carboxylic acid ester is prepared by reacting a fluoroalkyl silyl ketene acetal of the formula ##STR2## wherein R' is alkyl and R.sub.f and R are the same as defined above, with the corresponding acetal, ketone or acyl halide.

.alpha.-Fluoroalkyl carboxylic acid esters and process for preparing the

An alkylated or alkenylated malonic ester having a fluorine containing aliphatic substituent and derivatives thereof as expressed by the following general formula: ##STR1## where R.sub.f is a fluorine containing aliphatic group, R is an aliphatic group, or hydrogen or alkali metal atom, and R' is an unsubstituted or substituted aliphatic group. And a method to trap the enolate ion of a malonic ester having a fluorine containing aliphatic substituent as expressed by the following general formula,

Alkylated or alkenylated malonic acid or its derivatives having a

A fluoroalkyl silyl ketene acetal of the formula ##STR1## wherein R.sub.f is a fluoroalkyl group, and R and R' are the same or different and each is an alkyl group, which is prepared by reacting or fluorinated carboxylic acid of the formula

Growing community of inventors

Yokohama, Japan

Takeshi Nakai