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
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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)
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) |
-
1948
- 1948-12-15 CH CH289889D patent/CH289889A/en unknown
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