BE819099A - Thiazoline- azetidinone derivs - and their n-isopropylidene derivs, inters for penams and cephams - Google Patents
Thiazoline- azetidinone derivs - and their n-isopropylidene derivs, inters for penams and cephamsInfo
- Publication number
- BE819099A BE819099A BE147829A BE147829A BE819099A BE 819099 A BE819099 A BE 819099A BE 147829 A BE147829 A BE 147829A BE 147829 A BE147829 A BE 147829A BE 819099 A BE819099 A BE 819099A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- radical
- derivs
- formula
- carboxylic acid
- Prior art date
Links
- 150000001781 cephams Chemical class 0.000 title 1
- 150000002959 penams Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- -1 aralkyl radical Chemical class 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
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)
Abstract
Novel title cpds of formula (I): (where X is H or halogen R is H, OH, SH, lower alkylthio, azido, CN or opt. substd alkyl, aryl or aralkyl which may be interrupted by O or N; and Y is H or where Z is opt. salified or esterified COOH with the proviso that X and R are not simultaneously H). are prepd by treating a cpd of formula (II) with a base to give cpds in which X=H, Y=Z and Z=esterified COOH, or by treating (II) with an alkyl hypohalite to give cpds in which X=halogen.
Description
Intermédiaires pour la préparation de pénicillines et de
céphalosporines.
<EMI ID=1.1> <EMI ID=2.1>
<EMI ID=3.1>
et indique que ces composes sont d'utiles intermédiaires pour <EMI ID=4.1>
<EMI ID=5.1>
<EMI ID=6.1>
<EMI ID=7.1>
<EMI ID=8.1> <EMI ID=9.1>
X et R ne représentent pas simultanément des atomes d'hydrogène.
Lorsque,dans la formule, R représente un radical alkyle, aryle ou aralkyle éventuellement uni par un atone d'oxygène ou
d'azote, des: exemples de significations appropriées pour R sont
<EMI ID=10.1>
Des substituants éventuels appropriés pour ces radicaux
<EMI ID=11.1>
précités.
'Une signification préférée pour R est le radical
<EMI ID=12.1>
Une signification préférée pour X est l'atonie d'hydrogène. ou l'atome de chlore.
<EMI ID=13.1>
ou estérifié. Des exemples typiques de radicaux acide carboxylique estérifiés représentés par Z sont ceux qui sont facilement convertis en radicaux acide carboxylique libres,comme les radicaux ester t-butylique et p-méthoxybenzylique (tous deux élimi-
<EMI ID=14.1> <EMI ID=15.1> <EMI ID=16.1>
<EMI ID=17.1>
<EMI ID=18.1>
<EMI ID=19.1>
<EMI ID=20.1> semblable.
<EMI ID=21.1>
<EMI ID=22.1>
où R et Z sont comme défini à propos de la formule (I) et X représente un atone d'halogène par réaction de l'ester d'acide isocyanopénicillanique de formule (III) correspondant avec un hypohalogéni-te d'alkyle. A nouveau, on exécute de préférence
<EMI ID=23.1>
un hypohalogénite de t-butyle, confie l'hypochlorite de t-butyle.
<EMI ID=24.1>
l'ozone ou le tétroxyde d'osmium entre autres, en vue d'éliminer le radical isopropylldène substitue de l'atome d'azote du cycle
<EMI ID=25.1>
De plus, on peut désestérifier le couposé de foraule (IA) ou (IB) en vue de convertir le radical Z en un radical acide carboxylique libre, éventuellement salifié. Il est évident que, lorsqu'on désire obtenir finalement un tel acide.libre ou sel, on choisit le radical. acide carboxylique estérifié représenté par Z dans la formule -(III) du composé paroi ceux qui sont aisément convertis.
On peut obtenir les composés de départ de.formule (III) où R représente l'atome d'hydrogène par réaction du composé 6-for-
<EMI ID=26.1> <EMI ID=27.1>
<EMI ID=28.1>
<EMI ID=29.1>
<EMI ID=30.1>
<EMI ID=31.1>
<EMI ID=32.1>
<EMI ID=33.1> <EMI ID=34.1>
<EMI ID=35.1>
<EMI ID=36.1>
de carbonate de potassium en poudre et de 2,5 g d'acrylate de benzyle pendant 90 minutes. On ajoute de l'eau glacée, puis on extrait l'huile précipitée dans l'acétate d'Éthyle. On lave les extraits à l'eau, on les sèche et on les évapore. Par chronato-
<EMI ID=37.1>
<EMI ID=38.1>
<EMI ID=39.1>
<EMI ID=40.1>
d'eau glacée et extraction ].-acétate d'éthyle, on lave les
<EMI ID=41.1>
<EMI ID=42.1> ' <EMI ID=43.1>
Après addition de 10 ml d'eau glacée et extraction à l'acétate d'éthyle, on lave les extraits à l'eau, on les sèche et on les évapore. Par chromatographie sur une colonne de gel de silice,
<EMI ID=44.1>
<EMI ID=45.1>
<EMI ID=46.1>
<EMI ID=47.1> <EMI ID=48.1>
<EMI ID=49.1>
tion à l'acétate d'éthyle, on lave les extraits. à l'eau, on les
<EMI ID=50.1>
<EMI ID=51.1>
rassemble les .fractions contenant le dérivé chloré recherché et
<EMI ID=52.1>
<EMI ID=53.1>
<EMI ID=54.1>
<EMI ID=55.1>
<EMI ID=56.1>
<EMI ID=57.1>
<EMI ID=58.1>
<EMI ID=59.1>
<EMI ID=60.1>
<EMI ID=61.1>
rature ambiante pendant encore 90 minutes un mélange de 0,70 g
<EMI ID=62.1>
obtient par chromatographie sur une colonne de gel de silice avec
<EMI ID=63.1>
recherché sous forme d'un sirop jaune pale.
<EMI ID=64.1> <EMI ID=65.1> <EMI ID=66.1>
huile qui so solidifie dans l'éther de pétrole en un solide fon-
<EMI ID=67.1>
<EMI ID=68.1>
<EMI ID=69.1>
<EMI ID=70.1>
les extraits à l'eau, on les sèche et on les évapore,puis on soumet le résidu à une chromatographie sur gel de silice pour obte-
<EMI ID=71.1>
<EMI ID=72.1>
<EMI ID=73.1>
<EMI ID=74.1>
<EMI ID=75.1>
<EMI ID=76.1>
<EMI ID=77.1>
<EMI ID=78.1>
hept-2-ène
<EMI ID=79.1>
<EMI ID=80.1>
<EMI ID=81.1>
<EMI ID=82.1> . sion à 0[deg.]C pendant encore 1 heure. Après addition de saumure <EMI ID=83.1>
qu'à décoloration de la solution. On collecte la phase organique, on la lave- avec du bicarbonate de sodium dilue,avec de l'eau,
<EMI ID=84.1>
et on l'évapore. Par chronatographie de 0,7 g (100%) du résidu,
<EMI ID=85.1>
<EMI ID=86.1>
tate d'éthyle- et d'éther de pétrole.
<EMI ID=87.1>
<EMI ID=88.1>
<EMI ID=89.1>
<EMI ID=90.1>
<EMI ID=91.1>
<EMI ID=92.1>
<EMI ID=93.1>
l'atone d 'hydrogène ou un radical hydroxyle, mercapto, (alkyl in-
<EMI ID=94.1>
atone d'oxygène ou d'azote; et Y représente l'atone d'hydrogène
<EMI ID=95.1>
<EMI ID=96.1>
<EMI ID=97.1>
salifie ou estérifié, étant entendu que X et R ne représentent
<EMI ID=98.1>
Intermediates for the preparation of penicillins and
cephalosporins.
<EMI ID = 1.1> <EMI ID = 2.1>
<EMI ID = 3.1>
and indicates that these compounds are useful intermediates for <EMI ID = 4.1>
<EMI ID = 5.1>
<EMI ID = 6.1>
<EMI ID = 7.1>
<EMI ID = 8.1> <EMI ID = 9.1>
X and R do not simultaneously represent hydrogen atoms.
When, in the formula, R represents an alkyl, aryl or aralkyl radical optionally joined by an oxygen atom or
nitrogen, examples of suitable meanings for R are
<EMI ID = 10.1>
Suitable optional substituents for these radicals
<EMI ID = 11.1>
above.
'A preferred meaning for R is the radical
<EMI ID = 12.1>
A preferred meaning for X is hydrogen atony. or the chlorine atom.
<EMI ID = 13.1>
or esterified. Typical examples of esterified carboxylic acid radicals represented by Z are those which are easily converted to free carboxylic acid radicals, such as t-butyl ester and p-methoxybenzyl ester radicals (both removed.
<EMI ID = 14.1> <EMI ID = 15.1> <EMI ID = 16.1>
<EMI ID = 17.1>
<EMI ID = 18.1>
<EMI ID = 19.1>
Similar <EMI ID = 20.1>.
<EMI ID = 21.1>
<EMI ID = 22.1>
where R and Z are as defined with regard to formula (I) and X represents a halogen atom by reaction of the isocyanopenicillanic acid ester of formula (III) corresponding with an alkyl hypohalogenite. Again, it is preferable to perform
<EMI ID = 23.1>
t-butyl hypohalogenite, confides t-butyl hypochlorite.
<EMI ID = 24.1>
ozone or osmium tetroxide among others, in order to remove the isopropylldene radical substituted for the nitrogen atom of the ring
<EMI ID = 25.1>
In addition, it is possible to deesterify the coupose de foraule (IA) or (IB) in order to convert the radical Z into a free carboxylic acid radical, optionally salified. It is obvious that when it is desired to finally obtain such a free acid or salt, the radical is chosen. esterified carboxylic acid represented by Z in the formula - (III) of the compound wall those which are easily converted.
The starting compounds of formula (III) where R represents the hydrogen atom can be obtained by reaction of the compound 6-for-
<EMI ID = 26.1> <EMI ID = 27.1>
<EMI ID = 28.1>
<EMI ID = 29.1>
<EMI ID = 30.1>
<EMI ID = 31.1>
<EMI ID = 32.1>
<EMI ID = 33.1> <EMI ID = 34.1>
<EMI ID = 35.1>
<EMI ID = 36.1>
of powdered potassium carbonate and 2.5 g of benzyl acrylate for 90 minutes. Ice water is added, then the precipitated oil is extracted into ethyl acetate. The extracts are washed with water, dried and evaporated. By chronato-
<EMI ID = 37.1>
<EMI ID = 38.1>
<EMI ID = 39.1>
<EMI ID = 40.1>
of ice water and extraction] .- ethyl acetate, the
<EMI ID = 41.1>
<EMI ID = 42.1> '<EMI ID = 43.1>
After addition of 10 ml of ice-water and extraction with ethyl acetate, the extracts are washed with water, dried and evaporated. By chromatography on a column of silica gel,
<EMI ID = 44.1>
<EMI ID = 45.1>
<EMI ID = 46.1>
<EMI ID = 47.1> <EMI ID = 48.1>
<EMI ID = 49.1>
The extracts are washed with ethyl acetate. in the water, they are
<EMI ID = 50.1>
<EMI ID = 51.1>
gathers the .fractions containing the desired chlorinated derivative and
<EMI ID = 52.1>
<EMI ID = 53.1>
<EMI ID = 54.1>
<EMI ID = 55.1>
<EMI ID = 56.1>
<EMI ID = 57.1>
<EMI ID = 58.1>
<EMI ID = 59.1>
<EMI ID = 60.1>
<EMI ID = 61.1>
leave at room for another 90 minutes a mixture of 0.70 g
<EMI ID = 62.1>
obtained by chromatography on a column of silica gel with
<EMI ID = 63.1>
sought after in the form of a pale yellow syrup.
<EMI ID = 64.1> <EMI ID = 65.1> <EMI ID = 66.1>
oil which solidifies in petroleum ether to a molten solid.
<EMI ID = 67.1>
<EMI ID = 68.1>
<EMI ID = 69.1>
<EMI ID = 70.1>
the water extracts, dried and evaporated, then the residue is subjected to chromatography on silica gel to obtain
<EMI ID = 71.1>
<EMI ID = 72.1>
<EMI ID = 73.1>
<EMI ID = 74.1>
<EMI ID = 75.1>
<EMI ID = 76.1>
<EMI ID = 77.1>
<EMI ID = 78.1>
hept-2-ene
<EMI ID = 79.1>
<EMI ID = 80.1>
<EMI ID = 81.1>
<EMI ID = 82.1>. Zion at 0 [deg.] C for a further 1 hour. After addition of brine <EMI ID = 83.1>
only to discoloration of the solution. The organic phase is collected, washed with dilute sodium bicarbonate, with water,
<EMI ID = 84.1>
and we evaporate it. By chronatography of 0.7 g (100%) of the residue,
<EMI ID = 85.1>
<EMI ID = 86.1>
ethyl tate and petroleum ether.
<EMI ID = 87.1>
<EMI ID = 88.1>
<EMI ID = 89.1>
<EMI ID = 90.1>
<EMI ID = 91.1>
<EMI ID = 92.1>
<EMI ID = 93.1>
the atone of hydrogen or a hydroxyl, mercapto, (alkyl in-
<EMI ID = 94.1>
oxygen or nitrogen atone; and Y represents the hydrogen atone
<EMI ID = 95.1>
<EMI ID = 96.1>
<EMI ID = 97.1>
salifies or esterifies, it being understood that X and R do not represent
<EMI ID = 98.1>
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE147829A BE819099A (en) | 1974-08-22 | 1974-08-22 | Thiazoline- azetidinone derivs - and their n-isopropylidene derivs, inters for penams and cephams |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE819099 | 1974-08-22 | ||
| BE147829A BE819099A (en) | 1974-08-22 | 1974-08-22 | Thiazoline- azetidinone derivs - and their n-isopropylidene derivs, inters for penams and cephams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE819099A true BE819099A (en) | 1974-12-16 |
Family
ID=25648078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE147829A BE819099A (en) | 1974-08-22 | 1974-08-22 | Thiazoline- azetidinone derivs - and their n-isopropylidene derivs, inters for penams and cephams |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE819099A (en) |
-
1974
- 1974-08-22 BE BE147829A patent/BE819099A/en unknown
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