GB1281172A - Improved process for preparing 7-aminocephalosporanic acid - Google Patents

Improved process for preparing 7-aminocephalosporanic acid

Info

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
Application number
GB30674/69A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1281172A publication Critical patent/GB1281172A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D501/00Heterocyclic 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
    • C07D501/14Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/187-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
    • EFIXED CONSTRUCTIONS
    • E04BUILDING
    • E04FFINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
    • E04F21/00Implements for finishing work on buildings
    • E04F21/02Implements for finishing work on buildings for applying plasticised masses to surfaces, e.g. plastering walls
    • E04F21/06Implements for applying plaster, insulating material, or the like
    • E04F21/08Mechanical implements
    • E04F21/12Mechanical 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.
GB30674/69A 1968-06-19 1969-06-17 Improved process for preparing 7-aminocephalosporanic acid Expired GB1281172A (en)

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)

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