GB1111214A - Process for preparing semisynthetic penicilins - Google Patents
Process for preparing semisynthetic penicilinsInfo
- Publication number
- GB1111214A GB1111214A GB171366A GB171366A GB1111214A GB 1111214 A GB1111214 A GB 1111214A GB 171366 A GB171366 A GB 171366A GB 171366 A GB171366 A GB 171366A GB 1111214 A GB1111214 A GB 1111214A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cyanomethyl
- amino
- pyridine
- ether
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- -1 cyanomethyl ester Chemical class 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- ORFYDEOVHNVUCK-UHFFFAOYSA-N cyanomethyl 2-(phenylmethoxycarbonylamino)acetate Chemical compound N#CCOC(=O)CNC(=O)OCC1=CC=CC=C1 ORFYDEOVHNVUCK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229960002317 succinimide Drugs 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 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
6-Amino-penicillanic acids are acylated in the amino group by treatment with a cyanomethyl ester of the acylating acid. The reaction is suitably effected in an organic or organic-aqueous liquid medium, such as pyridine, acetone, or tetrahydrofuran, in the presence of a catalytic heterocyclic base, such as 2-hydroxy-pyridine, pyrazole, triazole, imidazole or succinimide, by reacting a penicillanic acid salt of a secondary or tertiary amine with a molar excess of the cyanomethyl ester. The product may be purified by extraction of by-products from its aqueous solution with ethyl acetate or ether at neutral or alkaline pH, followed by liberation of the acylated amine from its salt form by addition of acid, and extraction from the acidified aqueous solution with ethyl acetate or ether. The free acid is then precipitated from the solvent by addition of a base (e.g. triethylamine or ammonia) to give the solid salt. Examples are given for acylation of 6-aminopenicillanic acid using cyanomethyl carbobenzoxyamino-acetate, and cyanomethyl alpha-carbobenzoxy-L-amino-beta-phenyl propionate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL107011A PL53617B1 (en) | 1965-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111214A true GB1111214A (en) | 1968-04-24 |
Family
ID=19944472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB171366A Expired GB1111214A (en) | 1965-01-16 | 1966-01-13 | Process for preparing semisynthetic penicilins |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE675128A (en) |
| BR (1) | BR6676457D0 (en) |
| CH (1) | CH468407A (en) |
| DK (1) | DK125596B (en) |
| FR (1) | FR1463536A (en) |
| GB (1) | GB1111214A (en) |
| SE (1) | SE349813B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1062052B (en) * | 1968-11-08 | 1983-06-25 | Lorenzini Sas Inst Biochim | PROCESS FOR THE PRODUCTION OF 6 D ACID - PENICILLANIC ALPHA AMYOPHYLACETANID |
-
1966
- 1966-01-13 GB GB171366A patent/GB1111214A/en not_active Expired
- 1966-01-13 FR FR45755A patent/FR1463536A/en not_active Expired
- 1966-01-14 CH CH47666A patent/CH468407A/en unknown
- 1966-01-14 SE SE52166A patent/SE349813B/xx unknown
- 1966-01-14 BE BE675128D patent/BE675128A/xx unknown
- 1966-01-17 BR BR17645766A patent/BR6676457D0/en unknown
- 1966-01-17 DK DK25166A patent/DK125596B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6676457D0 (en) | 1973-09-06 |
| DK125596B (en) | 1973-03-12 |
| FR1463536A (en) | 1966-12-23 |
| CH468407A (en) | 1969-02-15 |
| SE349813B (en) | 1972-10-09 |
| BE675128A (en) | 1966-05-03 |
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