GB1281172A - Improved process for preparing 7-aminocephalosporanic acid - Google Patents
Improved process for preparing 7-aminocephalosporanic acidInfo
- Publication number
- GB1281172A GB1281172A GB30674/69A GB3067469A GB1281172A GB 1281172 A GB1281172 A GB 1281172A GB 30674/69 A GB30674/69 A GB 30674/69A GB 3067469 A GB3067469 A GB 3067469A GB 1281172 A GB1281172 A GB 1281172A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminocephalosporanic acid
- oxide
- added
- propiolactone
- aca
- 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
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
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
- E04F21/00—Implements for finishing work on buildings
- E04F21/02—Implements for finishing work on buildings for applying plasticised masses to surfaces, e.g. plastering walls
- E04F21/06—Implements for applying plaster, insulating material, or the like
- E04F21/08—Mechanical implements
- E04F21/12—Mechanical implements acting by gas pressure, e.g. steam pressure
Landscapes
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1281172 Preparing 7-aminocephalosporanic acid ELI LILLY & CO 17 June 1969 [19 June 1968 (2)] 30674/69 Heading C2A 7-Aminocephalosporanic acid is prepared by a process of reacting cephalosporin C or a salt thereof with a nitrosating agent, a carbocyclic arenediazonium salt or a compound that provides positive halogen, at a temperature below 60 C. in a solvent, and hydrolysing the resulting intermediate to give the 7-aminocephalosporanic acid, in which process an alkylene oxide containing 2 to 4 carbon atoms or #-propiolactone is added to the reaction mixture to obtain the 7- aminocephalosporanic acid. The alkylene oxide or propiolactone may be added to the hydrolysed reaction mixture resulting from treatment of the intermediate with water and/or a C 1 -C 3 alkanol, in which case its function is to precipitate the 7-aminocephalosporanic acid (7-ACA). Alternatively it may be added to the residue left after evaporating the reaction solvent before hydrolysis, when hydrolysis is brought about without the use of water and/or alkanol and 7- ACA is precipitated directly on adding the alkylene oxide or propiolactone. The reaction solvent is preferably a mixture of formic acid and nitroalkane with or without acetonitrile. Excess of the nitrosating agent, arenediazonium salt or compound providing halogen is preferably destroyed after the reaction, e.g. by adding ammonium sulphamate. Suitable alkylene oxides are ethylene oxide (i.e. oxirane), 1,2- propylene oxide, butene-1-oxide and butene-2- oxide. They may be added in a solvent, preferably all at once, suitable solvents being acetonitrile, ketones, esters, dioxane and tetrahydrofuran, which are poor solvents for the 7-ACA. 3-30 moles of alkylene oxide per mole of cephalosporin C starting material are used. Reference has been directed by the Comptroller to Specification 948858.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US73808468A | 1968-06-19 | 1968-06-19 | |
US73808568A | 1968-06-19 | 1968-06-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1281172A true GB1281172A (en) | 1972-07-12 |
Family
ID=27113310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30674/69A Expired GB1281172A (en) | 1968-06-19 | 1969-06-17 | Improved process for preparing 7-aminocephalosporanic acid |
Country Status (10)
Country | Link |
---|---|
AT (1) | AT292920B (en) |
BE (1) | BE734720A (en) |
CH (1) | CH513208A (en) |
DE (1) | DE1930956C3 (en) |
FR (1) | FR2011244A1 (en) |
GB (1) | GB1281172A (en) |
IE (1) | IE33374B1 (en) |
IL (1) | IL32407A (en) |
NL (1) | NL6909332A (en) |
SE (1) | SE369603B (en) |
-
1969
- 1969-06-17 GB GB30674/69A patent/GB1281172A/en not_active Expired
- 1969-06-17 IE IE828/69A patent/IE33374B1/en unknown
- 1969-06-17 IL IL32407A patent/IL32407A/en unknown
- 1969-06-18 BE BE734720D patent/BE734720A/xx unknown
- 1969-06-18 SE SE08648/69A patent/SE369603B/xx unknown
- 1969-06-18 NL NL6909332A patent/NL6909332A/xx unknown
- 1969-06-19 DE DE1930956A patent/DE1930956C3/en not_active Expired
- 1969-06-19 AT AT582469A patent/AT292920B/en not_active IP Right Cessation
- 1969-06-19 FR FR6920591A patent/FR2011244A1/fr not_active Withdrawn
- 1969-06-19 CH CH939769A patent/CH513208A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
SE369603B (en) | 1974-09-09 |
BE734720A (en) | 1969-12-18 |
DE1930956C3 (en) | 1974-01-03 |
IE33374B1 (en) | 1974-06-12 |
FR2011244A1 (en) | 1970-02-27 |
DE1930956B2 (en) | 1973-05-30 |
DE1930956A1 (en) | 1970-01-02 |
CH513208A (en) | 1971-09-30 |
AT292920B (en) | 1971-09-10 |
NL6909332A (en) | 1969-12-23 |
IL32407A0 (en) | 1969-08-27 |
IL32407A (en) | 1973-05-31 |
IE33374L (en) | 1969-12-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLNP | Patent lapsed through nonpayment of renewal fees |