BE756806A - Process for 6-(d(-)-alpha-amino-phenylacet- - amido)-penicillanic acid - Google Patents
Process for 6-(d(-)-alpha-amino-phenylacet- - amido)-penicillanic acidInfo
- Publication number
- BE756806A BE756806A BE756806DA BE756806A BE 756806 A BE756806 A BE 756806A BE 756806D A BE756806D A BE 756806DA BE 756806 A BE756806 A BE 756806A
- Authority
- BE
- Belgium
- Prior art keywords
- alpha
- phenylacet
- amido
- amino
- penicillanic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 abstract 1
- 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
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000002955 isolation Methods 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-APA is acylated with D(-)alpha-aminophenylacetic acid protected by reaction with a beta-keto ester, a beta-dicarboxylic acid or O-nitrophenylsulphenyl chloride in an organic solvent at pH 8-10 at 20-80 degrees C. As the product hydrolysed in aq. acetone pref. at pH 2-3.5, evapd., the residue extd. with an organic solvent, pref. BuOAc and the title product (I) isolated. (I) is a broad spectrum anti-biotic and is produced by a simple procedure without isolation of intermediates.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE756806 | 1970-09-29 | ||
| FR7036023A FR2109178A5 (en) | 1970-09-29 | 1970-10-06 | Process for 6-(d(-)-alpha-amino-phenylacet- - amido)-penicillanic acid |
| GB4987370A GB1332508A (en) | 1970-09-29 | 1970-10-21 | Method for obtaining 6-d- alpha-amino-phenylacetamido- penicillanic acid |
| DE19702053214 DE2053214A1 (en) | 1970-09-29 | 1970-10-29 | Process for 6-(d(-)-alpha-amino-phenylacet- - amido)-penicillanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE756806A true BE756806A (en) | 1971-03-29 |
Family
ID=10453845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE756806D BE756806A (en) | 1970-09-29 | Process for 6-(d(-)-alpha-amino-phenylacet- - amido)-penicillanic acid |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE756806A (en) |
| DE (1) | DE2053214A1 (en) |
| FR (1) | FR2109178A5 (en) |
| GB (1) | GB1332508A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190897B (en) * | 1982-06-29 | 1988-02-24 | Opos Biochimica Srl | PROCEDURE FOR THE PREPARATION OF THE 1-ETHOXYCARBONYLOXYETHYL ACID ACID 6- (D (-) - ALPHA AMINOALPHA-PHENYLACETAMIDE) -PENICILLANIC |
-
0
- BE BE756806D patent/BE756806A/en unknown
-
1970
- 1970-10-06 FR FR7036023A patent/FR2109178A5/en not_active Expired
- 1970-10-21 GB GB4987370A patent/GB1332508A/en not_active Expired
- 1970-10-29 DE DE19702053214 patent/DE2053214A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2053214A1 (en) | 1972-05-10 |
| GB1332508A (en) | 1973-10-03 |
| FR2109178A5 (en) | 1972-05-26 |
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