CS258291B1 - Hydrochlorides (Z) -2-alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl chloride - Google Patents

Abstract

The solution relates to hydrochlorides of (Z)-2- -alkoxyimino-2-[2-(4-aminobenzenesulfonamido)-4-thiazolyl] acetyl chlorides of general formula I, new substances useful as intermediates in the synthesis of a new group of beta-lactam antibiotics. These new substances are amenable to the reaction of (Z)-2- -alkoxyimino-2-[2-(4-aminobenzenesulfonamido)-4-thiazolyl] acetic acids with phosphorus pentachloride.

Description

The present invention relates to (Z) -2-alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl chloride hydrochlorides of the formula I

wherein R is C 1 -C 2 alkyl. These novel, yet undescribed substances are essential intermediates in the synthesis of a new class of semisynthetic beta-lactam antibiotics, the structure of which contains (Z) -2-alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl.

The compounds of the formula I according to the invention can be prepared by methods known from the literature, for example by reacting (Z) -2-alkoxyimino- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetic acids with phosphorus pentachloride, optionally in the presence of a catalytic amount of dimethylformamide. Acetonitrile is preferably used as the medium and the reaction is carried out at a temperature of -40 to 60 ° C, preferably at a temperature of -40 to 0 ° C.

Further details of the preparation of the compounds according to the invention are given in the following examples. It goes without saying that, in addition to the above process, other alternatives leading to the desired compounds of the formula I are possible, which are common to the person skilled in the art and do not have to be explicitly named.

Example 1

2- [2- (4-Aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-methoxyiminoacetyl chloride hydrochloride

To a suspension of 2 g (0.006 mol) of 2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-methoxyiminoacetic acid in 10 ml of anhydrous acetonitrile was added a drop of dimethylformamide with stirring and cooling to -25 ° C. and 2.2 g (0.01 mol) of phosphorus pentachloride. The solution formed after stirring for 15 minutes without cooling is cooled to -40 ° C and the precipitated product is filtered off with suction after 10 minutes and washed with anhydrous benzene and hexane. After drying under vacuum at 60 ° C, 1.2 g (52%) of a yellowish product are obtained which decomposes when heated above 190 ° C. Chlorine content (argentometric ky) 104.2 4 calculated amount.

Example 2

2- [2- (4-Aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-ethoxyiminoacetyl chloride hydrochloride

Following the procedure described in Example 1, using an equivalent amount of ethoxy derivative in 34.9% yield, the title compound is obtained as a yellowish product which decomposes when heated above 180 ° C. Chlorine content (argentometric) 97.6 4 of the calculated amount.

Claims (1)

object of the invention (Z) -2-alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl chloride hydrochlorides of formula (I): wherein R is C 1 -C 2 alkyl.