SU108808A2 - The method of obtaining d11-threo-1-para-nitrophenyl-2-amino-1,3-propane diol - Google Patents

Description

In fiBT. St. Or 106358 described method poluchenn d; -tre-1-para-nitrophenyl-; -amino-1, 3 pro-ol (ol) (treoamip), concludes with the result that the residue obtained after removing the alumina compounds and distilling the solvent from the reaction of the Hoii mass from the reduction of d, jpara-nitro-7. - acetylami o - ;; - hydroxypropio: | 1ene.) on aluminum isopropylate, directly processed (o.my, -1) t) t) with aqueous solution of mineral acids, mine release stage d, / -treo-1-para-nitrofeiyl-2-acet tamn-1,3-iroandio.-1a.

It has been established that the resulting threoamine is sufficiently pure for irevrai, it is synthomycin, but not I1) igoden, without the addition of very good; 1), whether it is obtained from an organ, because of the presence of the hemoglobin: vnno-acidic co.ief.

With a goal;) ustangans;.; This residue node, i.e., for the iosyiis and quality of the treoamine and the simplification of the technological process, is proposed to wash the above residue (i.e., d, l-threo1-para-nitrafenil-2-acetlamine1, -nronanediol) in the environment of isopropyl alcohol. As a result, only threoamine hydrochloride is released in the reaction mass, and the organic impurities present in the starting material remain completely in the mother liquor. Example I. To a solution of aluminum isopropium aluminum prepared from 12.7 g of aluminum and 2.50 ml of absolute iso-propane ga, add 50 g of d,; -para-nitro-a-acetyl SHO-3 oxpronnophenone and mix for 5 hours. iri 58-62. After that, iribavl 300 ml of 80 / o-isoicoanol, dries for 1 hour, cooled and coagulated at 46--52, consisting of nz 20 ml of 96% sulfuric acid, 20 g of sul (liaia kali ii 80 MI of water. After discharging Hiiie alum is filtered, extract ThpariijiyioT in 2 steps 800 .yl

80 ° / iso isopropanol, and the combined filtrates are evaporated in vacuo. To the residue were added 50 ml of absolute isopropanol, 70 mg of concentrated hydrochloric acid or equivalent ko, the amount of isonronanol saturated with chlorine, with hydrogen, and the reaction mixture was stirred at 70-75 for 1 hour. After completion of the reaction, the reaction mixture is cooled to 0.5 ° and stirring is continued at this temperature for 2 hours. The resulting hydrochloride d, /; -treo-1-para-nitrophenyl-2-amino-1,3-propandnol is filtered off, washed with 50 ml of absolute isopropanol and then with 60 ml of dichloroethane. If a sample is taken, hydrochloride, while stirring in a test tube with dichloroethane, smears it wet, then washing with dichloroethane is repeated once more. Hydrochloride d, (-treo-1-para-n1ggrofeiyl2-amino-1, 3-propanediol is dissolved when heated in 90 ml codes, process the carbon m solution (2-4 g), filter and after cooling to 35--38 The base of treoamine is precipitated by addition), of a sodium hydroxide solution.

Yield 22 g (53 ,, calculated on d, i para-nitro-a-acetylamino - p - hydroxyprocyophenone), so pl. 138.

Example 2. The process is carried out as described in Example I with the following changes:

a) Before adding the hydroxy ketone to the solution of nopropylate alumi or upHCaB.iHioT 27 ml of 10, .. - aqueous solution of chlorine) isto1-o hydrogen in absolute isoiropanol; b) oxyketone is added to the reaction mixture portions; m ;; 10 g after 30 lpig. each, after cheg.) after July 4, is kept for 3 hours at 58-62 and c) Yersd is coagulated into the reaction mass, 4 g of soda is added to the reaction mixture.

The output of d.i -treo-1-para-nitrophene; 1 l of 2-am11no-1,3-iropapdiol 29.5 g (theory) t. Pl. 138--139.

Example 3: The process is carried out as described in example 1 with the following changes: a) 24.3 grams of aluminum and 300 L1L of absolute isopropiol are taken to obtain an aluminum isoprone solution; b) oxyketone is introduced into the reaction mass in portions of 10 g, after 30 memes. each, which it ate for 3 hours ;; sa at 58-62 and c) the amount of coagulum is doubled.

The output of d, i-trso-1-nara-nptrofenyl-2-amino-1, 3-propaidiol 28.5 g (68Vo theory), so pl. 138-139.

Subject invention

The method of obtaining d, l -treo-1-para-nitrophenyl-2-amino-1,3-propanediol according to ed. St. Ln 106358, that is, in order to simplify the process and improve the quality of the product, saponification d; threo-1-para-nitrophenyl-2-acetyl-i-i. o-propanediol is produced in isopropyl alcohol.