GB1119806A - Process for the manufacture of 7-amino-cephalosporanic acid - Google Patents
Process for the manufacture of 7-amino-cephalosporanic acidInfo
- Publication number
- GB1119806A GB1119806A GB4310765A GB4310765A GB1119806A GB 1119806 A GB1119806 A GB 1119806A GB 4310765 A GB4310765 A GB 4310765A GB 4310765 A GB4310765 A GB 4310765A GB 1119806 A GB1119806 A GB 1119806A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- cephalosporanic acid
- solvent
- iminoether
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- -1 imide chloride Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/69—Sulfur trioxide; Sulfuric acid
- C01B17/74—Preparation
- C01B17/76—Preparation by contact processes
- C01B17/78—Preparation by contact processes characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
7-Amino-cephalosporanic acid of formula <FORM:1119806/C2/1> is prepared (a) by reacting N,N-phthaloyl cephalosporin C dibenzhdryl ester with phosphorus pentachloride, (b) converting the resulting imide chloride into a corresponding C1- 5 alkyl iminoether, (c) hydrolysing the iminoether with water in an acidic medium, hydrolysing the resulting 7-amino-cephalosporanic acid benzhyryl ester with trifluoracetic acid in the presence of anisole, converting the trifluoracetic acid to trifluoracetate with a tertiary amine in a polar solvent and crystallizing the 7-amino-cephalosporanic acid from the solvent. Methylene chloride is used as chief solvent; step (a) is carried out in the presence of a tertiary amine e.g. pyridine at - 20 DEG to - 10 DEG C.; step (b) requires a large excess of alcohol; step (c) may be carried out with aqueous hydrochloric acid.
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199263A CH433316A (en) | 1963-02-18 | 1963-02-18 | New process for the production of 7-aminocephalosporan compounds |
| CH267563A CH504471A (en) | 1963-11-25 | 1963-03-01 | 7-Amino-cephalosporanic acid derivs |
| CH424963 | 1963-04-03 | ||
| CH735863 | 1963-06-13 | ||
| CH824663 | 1963-07-02 | ||
| CH1211263 | 1963-10-02 | ||
| CH1360063 | 1963-11-06 | ||
| CH73064 | 1964-01-22 | ||
| DK72864A DK118506B (en) | 1963-02-18 | 1964-02-14 | Process for the preparation of 7-aminocephalosporanic acid or esters thereof. |
| CH1316664A CH467803A (en) | 1963-02-18 | 1964-10-09 | New process for the production of 7-aminocephalosporanic acid |
| CH1469664 | 1964-11-13 | ||
| DK516765A DK141847B (en) | 1964-02-14 | 1965-10-08 | Process for the preparation of 7-amino-cephalosporanoic acid. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1119806A true GB1119806A (en) | 1968-07-10 |
Family
ID=27582877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4310765A Expired GB1119806A (en) | 1963-02-18 | 1965-10-11 | Process for the manufacture of 7-amino-cephalosporanic acid |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1119806A (en) |
| NL (1) | NL148610B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562253A (en) * | 1982-08-06 | 1985-12-31 | Biochemie Gesellschaft M.B.H. | Deacylation of amides |
-
1965
- 1965-10-08 NL NL6513095A patent/NL148610B/en unknown
- 1965-10-11 GB GB4310765A patent/GB1119806A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562253A (en) * | 1982-08-06 | 1985-12-31 | Biochemie Gesellschaft M.B.H. | Deacylation of amides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL148610B (en) | 1976-02-16 |
| NL6513095A (en) | 1966-04-12 |
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