SU386931A1 - METHOD FOR PREPARING AMIDES 2,2-DIMETHYL-3-ACETYLAMINOCYCLOBUTYLACACIC ACID - Google Patents

Description

one

The present invention relates to the preparation of new amides with 2,2-dimethyl-3-a with cetyl-1-ON-cyclobutyl-acetic acid, which can be used as a physiological active compound.

It is known that when treating oximes with acid, .on-example polyphosphate,. When heated, rearrangement of oximes into amides occurs.

The proposed compound. Co6 makes it possible to obtain new compounds — 2,2-dimethyl-3-acetal-aminocyclobutyl-aceonic acid amides, which have valuable properties for the pharmaceutical industry.

The method consists in that OXIM amide / -g {ys- | PINO "oic acid, containing an aliphatic, alicyclic or aromatic substituent in the amide rod, is treated with polyphosphoric acid at 95-100 ° C, followed by isolation of the target (Product by a known method.

The proposed method makes it possible to obtain amides of 2,2-dimethyl-3-acetylamino-2-Slobut (Iluxus ACID with a yield of 58-93.5%.

Example 1. N-β-Butylamide-2,2-dnmethyl-3 acetylaminocyclogluglyacetic acid.

A mixture consisting of 3.0 g of oxime N-n-butylamide / -th isopionic acid and 50 g of polyphosphoric acid is heated for

1.5 hours Ave. and 95-100 ° C. After cooling, the reaction mixture is poured into 100 ml of water and extracted with chloroform. The chloroform solution is dried over anhydrous magnesium sulphate. The solvent is distilled off in a vacuum, the residue is recrystallized from a mixture of n-hexap. And ethyl acetate (1: 1) to obtain 2.3 g (75.0%) of N-n-butylamide 2,2-dimethyl3-acetylaminocyclobutyl-acetic acid, m.p. . 125 - 126 ° C.

Found,%: N 11.07.

Ci4H2eO2N2

Calculated,%: N 11.01.

IR spectrum,. 3271, 3072 (VNH); 1637 (); 1551 (P amide band).

Example 2. Cyclohexylamide 2,2-dimethylZ-acetylaminocyclobutyl acetic acid.

Yield 58.1%; m.p. 167-168 ° C. Found,%: N 10.28.

Cl6H28O2N2

Calculated,%: N 10.00.

IR-CWCT | p, hedgehog-: 3292, 3073 (VNH); 1641 (); 1549 (P amide (Band). Example 3. p-Anisidyl 2,2-dimethyl-3-acetylaminocyclobutyl acetic acid. Yield 93.5%. M.P. 168-169 ° C. Found:%: N 9.03.

С17Н240зМ2.

Calculated,%: N 9.2.

IR-shezht.r, el-: 3362, 3310, 3204, 3158 (VNH); 1667, 1650 (); 1539 (P amide band).

Example 4. Piperazide 2,2-dimethyl-3-a: cethylamine clobutylsuonic acid.

Yield 70.0%; m.p. 212-214 ° C.

Found%: -N 13.15.

C24H4gO N4.

Calculated,%: N 12.93. IR infrared, 3363, 3082 (VNH); 1649, 1632 (); 1533 (P amide band).

Subject invention

An o-amide of 2,2-dimethyl-zachastilaminocyclobutyl-acetic acid is characterized in that the oxime amide dl-t uc-inH of onoic acid, containing the IB amide group of an aliphatic, alicyclic or aromatic substituent, is treated with polyphosphoric acid; -100 ° C, followed by separation of the target product from;