CH289889A - Process for preparing an aromatic acylamidodiol. - Google Patents

Process for preparing an aromatic acylamidodiol.

Info

Publication number
CH289889A
CH289889A CH289889DA CH289889A CH 289889 A CH289889 A CH 289889A CH 289889D A CH289889D A CH 289889DA CH 289889 A CH289889 A CH 289889A
Authority
CH
Switzerland
Prior art keywords
partial hydrolysis
aromatic
subjected
acylamidodiol
preparing
Prior art date
Application number
Other languages
French (fr)
Inventor
Company Parke Davis
Original Assignee
Parke Davis & Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Parke Davis & Co filed Critical Parke Davis & Co
Publication of CH289889A publication Critical patent/CH289889A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring

Description

  

  Procédé de préparation     d'un        acylamidodiol        aromatique.       Dans le brevet principal, on a décrit un  procédé de préparation du     !U-1-phényl-2-acét-          amidopropane-1,3-diol.     



  Le présent brevet a pour objet un procédé  de préparation d'un autre     acylamidodiol    aro  matique.  



  Ce procédé est caractérisé en ce que l'on  soumet à une hydrolyse partielle, dans des  conditions aqueuses, la forme structurale        pseudo     d'un     aminodiol        triacylé    de formule  
EMI0001.0010     
    dans laquelle Ri et     R3    sont des radicaux  acyle, et dans des conditions telles qu'il se  forme le     !U-1-phényl-2-dichloroacétamidopro-          pane-1,3-diol.     



  Ce composé est une nouvelle substance  cristallisée présentant un point de fusion de  95-96  C (forme racémique).  



  De préférence, on effectue l'hydrolyse par  tielle au moyen d'un hydroxyde d'un métal  alcalin dissous dans une solution aqueuse con  tenant un solvant organique miscible avec l'eau.  D'ordinaire, on soumet à ladite hydrolyse la       forme    racémique (dl) du     P-1-phényl-2-di-          ehloroacétamido-1,3-diacétoxypropane.    La tem  pérature est avantageusement maintenue en  dessous de 50  C et il est préférable d'uti  liser comme solvant organique miscible avec  l'eau une cétone aliphatique telle que l'acétone    ou un alcool miscible avec l'eau tel que l'alcool  éthylique. Les meilleurs résultats sont obtenus  à l'aide d'une solution aqueuse à<B>500/a</B> du sol  vant organique miscible avec l'eau.  



  Le produit obtenu par le procédé selon  l'invention est un produit intermédiaire pour  la préparation de composés ayant une activité  antibiotique.  



  <I>Exemple:</I>  On dissout 750 mg de     dl-#u-1-phényl-2-          dichloroacétamido-1,3-diacétoxypropane    dans  100     em3    d'acétone. On y ajoute ensuite 50     em3     d'une solution 0,1 n de     NaOH    et on laisse repo  ser le mélange pendant une heure, à 0  C. La  solution est ensuite neutralisée avec de l'acide  sulfurique 0,1 n, évaporée à siccité et le résidu  est extrait avec de l'acétate d'éthyle. On filtre  l'extrait et on distille l'acétate d'éthyle dans  le vide.

   On recristallise le résidu dans de l'acé  tate d'éthyle pour obtenir le     dl-P-1-phényl-2-          dichloroacétamidopropane-1,3-diol    recherché;  ce produit, de point de fusion 95-96  C, ré  pond à la formule  
EMI0001.0024     




  Process for preparing an aromatic acylamidodiol. In the main patent, a process for the preparation of! U-1-phenyl-2-acet-amidopropane-1,3-diol has been described.



  The present patent relates to a process for preparing another aromatic acylamidodiol.



  This process is characterized in that the pseudo structural form of a triacylated aminodiol of formula is subjected to partial hydrolysis, under aqueous conditions.
EMI0001.0010
    wherein R 1 and R 3 are acyl radicals, and under conditions such that! U-1-phenyl-2-dichloroacetamidopropane-1,3-diol is formed.



  This compound is a new crystalline substance with a melting point of 95-96 C (racemic form).



  Preferably, the partial hydrolysis is carried out by means of a hydroxide of an alkali metal dissolved in an aqueous solution containing an organic solvent miscible with water. Usually, the racemic form (dl) of P-1-phenyl-2-di-ehloroacetamido-1,3-diacetoxypropane is subjected to said hydrolysis. The temperature is advantageously maintained below 50 ° C. and it is preferable to use as organic solvent miscible with water an aliphatic ketone such as acetone or an alcohol miscible with water such as ethyl alcohol. The best results are obtained using an aqueous solution of <B> 500 / a </B> of organic soil miscible with water.



  The product obtained by the process according to the invention is an intermediate product for the preparation of compounds having antibiotic activity.



  <I> Example: </I> 750 mg of dl- # u-1-phenyl-2-dichloroacetamido-1,3-diacetoxypropane are dissolved in 100 em3 of acetone. Then 50 em3 of a 0.1 n NaOH solution are added and the mixture is left to stand for one hour at 0 C. The solution is then neutralized with 0.1 n sulfuric acid and evaporated to dryness. and the residue is extracted with ethyl acetate. The extract is filtered and the ethyl acetate is distilled off in vacuo.

   The residue is recrystallized from ethyl acetate to give the desired dl-P-1-phenyl-2-dichloroacetamidopropane-1,3-diol; this product, with a melting point of 95-96 C, corresponds to the formula
EMI0001.0024

Claims (1)

REVENTDICATION: Procédé de préparation d'un acylamido- diol aromatique, caractérisé en ce que l'on soumet à une hydrolyse partielle, dans des conditions aqueuses, la forme structurale pseudo d'un aminodiol triacylé de formule EMI0002.0004 dans laquelle Ri et R3 sont des radicaux acyle et dans des conditions telles qu'il se forme le P -1-phényl-2 - dichloroacétamidopropane-1, CLAIM: Process for the preparation of an aromatic acylamidediol, characterized in that the pseudo structural form of a triacylated aminodiol of formula is subjected to partial hydrolysis, under aqueous conditions. EMI0002.0004 in which R 1 and R 3 are acyl radicals and under conditions such that P -1-phenyl-2 - dichloroacetamidopropane-1 is formed, 3- diol. Ce produit est une substance cristallisée ayant un point de fusion de 95-96 C. SOUS-REVENDICATIONS 1. Procédé selon la revendication, caracté risé en ce que l'on soumet à ladite hydrolyse partielle la forme racémique (dl) dudit com posé aminodiol triacylé. 2. Procédé selon la revendication, earacté- ris6 en ce que ladite hydrolyse partielle est effectuée au moyen d'un hydroxyde d'un mé tal alcalin dissous dans une solution aqueuse contenant un solvant organique miscible avec l'eau. 3- diol. This product is a crystalline substance having a melting point of 95-96 C. SUB-CLAIMS 1. Process according to claim, characterized in that the racemic form (dl) of said aminodiol compound is subjected to said partial hydrolysis. triacylated. 2. A method according to claim, characterized in that said partial hydrolysis is carried out using a hydroxide of an alkali metal dissolved in an aqueous solution containing an organic solvent miscible with water.
CH289889D 1948-03-16 1948-12-15 Process for preparing an aromatic acylamidodiol. CH289889A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US289889XA 1948-03-16 1948-03-16
CH283750T 1948-12-15

Publications (1)

Publication Number Publication Date
CH289889A true CH289889A (en) 1953-03-31

Family

ID=25732283

Family Applications (1)

Application Number Title Priority Date Filing Date
CH289889D CH289889A (en) 1948-03-16 1948-12-15 Process for preparing an aromatic acylamidodiol.

Country Status (1)

Country Link
CH (1) CH289889A (en)

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