DE1178434B - Process for the separation of 6-aminopenicillanic acid and ª ‡ -aminobenzylpenicillin - Google Patents
Process for the separation of 6-aminopenicillanic acid and ª ‡ -aminobenzylpenicillinInfo
- Publication number
- DE1178434B DE1178434B DEF37739A DEF0037739A DE1178434B DE 1178434 B DE1178434 B DE 1178434B DE F37739 A DEF37739 A DE F37739A DE F0037739 A DEF0037739 A DE F0037739A DE 1178434 B DE1178434 B DE 1178434B
- Authority
- DE
- Germany
- Prior art keywords
- aminobenzylpenicillin
- aminopenicillanic acid
- separation
- trialkylamine
- announced
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Trennung von 6-Aminopenicillansäure und a-Aminobenzylpenicillin Verfahren zur Trennung von 6-Aminopenicillansäure und a-Aminobenzylpenicillin wurden bisher nicht beschrieben.Process for the separation of 6-aminopenicillanic acid and α-aminobenzylpenicillin Methods for the separation of 6-aminopenicillanic acid and α-aminobenzylpenicillin have been published not yet described.
Bei der Herstellung von a-Aminobenzylpenicillin kann, je nach der Art des gewählten Darstellungsverfahrens, das Problem auftreten, aus dem Reaktionsprodukt die nicht umgesetzte 6-Aminopenicillan säure zu entfernen. Da diese beiden Substanzen in ihren Löslichkeitseigenschaften einander sehr ähnlich sind, ist eine solche Trennung sehr schwer zu erreichen. In the production of α-aminobenzylpenicillin can, depending on the Type of preparation method chosen, the problem will arise from the reaction product to remove the unreacted 6-aminopenicillanic acid. Because these two substances One such separation is very similar in their solubility properties very difficult to get to.
Es wurde nun gefunden, daß man a-Aminobenzylpenicillin und 6-Aminopenicillansäure dadurch leicht trennen kann, daß man das Gemisch dieser beiden Substanzen in einem organischen Lösungsmittel suspendiert, die Suspension auf etwa 0°C abkühlt, dann pro Mol a-Aminobenzylpenicillin 1 Mol eines Trialkylamins zugibt und dann bei 0°C einige Stunden (etwa 5 Stunden) rührt. Hierbei geht das a-Aminobenzylpenicillin als Triäthylaminsalz in Lösung, während die 6-Aminopenicillansäure ungelöst bleibt und durch Filtration entfernt wird. Das Filtrat dampft man schonend ein und erhält dadurch das a-Aminobenzylpenicillin als praktisch reines Trialkylaminsalz. It has now been found that one can use α-aminobenzylpenicillin and 6-aminopenicillanic acid can easily be separated by combining these two substances in one Suspended organic solvent, the suspension is cooled to about 0 ° C, then 1 mole of a trialkylamine is added per mole of a-aminobenzylpenicillin and then at 0.degree stir for a few hours (about 5 hours). This is where the a-aminobenzylpenicillin goes as triethylamine salt in solution, while 6-aminopenicillanic acid remains undissolved and removed by filtration. The filtrate is gently evaporated and obtained thereby the a-aminobenzylpenicillin as a practically pure trialkylamine salt.
Als organische Lösungsmittel eignen sich Methylenchlorid, Chloroform, Methanol, Dimethylformamid, Formamid, Aceton, Acetonitril, Äthanol, Dimethylsulfoxyd, Glykolmonomethyläther. Besonders bewährt haben sich Methylenchlorid und Chloroform. Suitable organic solvents are methylene chloride, chloroform, Methanol, dimethylformamide, formamide, acetone, acetonitrile, ethanol, dimethyl sulfoxide, Glycol monomethyl ether. Methylene chloride and chloroform have proven particularly useful.
Unter den Trialkylaminen hat sich besonders das Triäthylamin bewährt, aber auch Trimethylamin, Methyldiäthylamin, Tripropylamin usw. sind geeignet. Among the trialkylamines, triethylamine has proven particularly useful, but trimethylamine, methyldiethylamine, tripropylamine, etc. are also suitable.
Im Hinblick auf die Tatsache, daß sich sowohl a-Aminobenzylpenicillin als auch 6-Aminopenicillansäure in einem Gemisch aus Methylenchlorid und Triäthylamin lösen, war es völlig überraschend und unvorhersehbar, daß sich aus einem Gemisch von 1 Moläquivalent 6-Aminopenicillansäure, 1 Moläquivalent a-Aminobenzylpenicillin und 1 Moläquivalent Triäthylamin nur das Salz des or-Aminobenzylpenicillins und nicht das der 6-Aminopenicillansäure in Methylenchlorid löst. In view of the fact that both a-aminobenzylpenicillin as well as 6-aminopenicillanic acid in a mixture of methylene chloride and triethylamine solve it was completely surprising and unpredictable to get out of a mixture of 1 molar equivalent of 6-aminopenicillanic acid, 1 molar equivalent of α-aminobenzylpenicillin and 1 molar equivalent of triethylamine only the salt of or-aminobenzylpenicillin and 6-aminopenicillanic acid does not dissolve in methylene chloride.
Beispiel Ein Gemisch von 1, 75 g a-Aminobenzylpenicillin (Wirksamkeit gegen bacterium subtilis = 1500 E) und 1, 08 g 6-Aminopenicillansäure wird in 40ccm absolutem Methylenchlorid suspendiert, die Suspension auf etwa 0°C abgekühlt, und 0,505 g Triäthylamin werden zugegeben. Anschließend wird 5 Stunden bei 0°C gerührt, der vorhandene Rückstand abgesaugt, mit Methylenchlorid gewaschen und getrocknet. Example A mixture of 1.75 g of a-aminobenzylpenicillin (effectiveness against bacterium subtilis = 1500 E) and 1.08 g of 6-aminopenicillanic acid is in 40ccm absolute Suspended methylene chloride, the suspension cooled to about 0 ° C, and 0.505 g Triethylamine are added. The mixture is then stirred at 0 ° C for 5 hours, the any residue is suctioned off, washed with methylene chloride and dried.
Ausbeute an 6-Aminopenicillansäure: 1,02 g, Wirksamkeit gegen bacterium subtilis = 130 E.Yield of 6-aminopenicillanic acid: 1.02 g, activity against bacterium subtilis = 130 E.
Das Filtrat des Niederschlages wird im Rotationsverdampfer völlig eingedampft und der Rückstand, das Triäthylaminsalz des a-Aminobenzylpenicillins, getrocknet. Ausbeute: 2,1 g (93, 4°/0 der Theorie), Wirksamkeit gegen bacterium subtilis, umgerechnet auf freies a-Aminobenzylpenicillin = 1550 E. The filtrate of the precipitate is completely in the rotary evaporator evaporated and the residue, the triethylamine salt of a-aminobenzylpenicillin, dried. Yield: 2.1 g (93.4% of theory), activity against bacterium subtilis, converted to free a-aminobenzylpenicillin = 1550 E.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF37739A DE1178434B (en) | 1962-09-04 | 1962-09-04 | Process for the separation of 6-aminopenicillanic acid and ª ‡ -aminobenzylpenicillin |
| CH1040963A CH429733A (en) | 1962-09-04 | 1963-08-23 | Method for the isolation and purification of ampicillin |
| GB3404063A GB994402A (en) | 1962-09-04 | 1963-08-28 | Process for the separation of 6-aminopenicillanic acid and ampicillin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF37739A DE1178434B (en) | 1962-09-04 | 1962-09-04 | Process for the separation of 6-aminopenicillanic acid and ª ‡ -aminobenzylpenicillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1178434B true DE1178434B (en) | 1964-09-24 |
Family
ID=7097031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF37739A Pending DE1178434B (en) | 1962-09-04 | 1962-09-04 | Process for the separation of 6-aminopenicillanic acid and ª ‡ -aminobenzylpenicillin |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1178434B (en) |
| GB (1) | GB994402A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5916762A (en) * | 1995-03-31 | 1999-06-29 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| BE1009264A3 (en) * | 1995-03-31 | 1997-01-07 | Dsm Nv | Process for the extraction of ampicillin. |
| EP0997199A1 (en) * | 1998-10-26 | 2000-05-03 | Dsm N.V. | Method for separation of solid compounds in suspension |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE607886A (en) * | 1960-09-06 | 1962-03-06 | Pfizer & Co C | Improvements in processes for separating amphoteric amino acids from their aqueous solutions |
-
1962
- 1962-09-04 DE DEF37739A patent/DE1178434B/en active Pending
-
1963
- 1963-08-28 GB GB3404063A patent/GB994402A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE607886A (en) * | 1960-09-06 | 1962-03-06 | Pfizer & Co C | Improvements in processes for separating amphoteric amino acids from their aqueous solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| GB994402A (en) | 1965-06-10 |
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