EP0038626A1 - Procédé de réduction électrolytique de céphalosporine p-nitrobenzyl-esters - Google Patents

Procédé de réduction électrolytique de céphalosporine p-nitrobenzyl-esters Download PDF

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Publication number
EP0038626A1
EP0038626A1 EP81301187A EP81301187A EP0038626A1 EP 0038626 A1 EP0038626 A1 EP 0038626A1 EP 81301187 A EP81301187 A EP 81301187A EP 81301187 A EP81301187 A EP 81301187A EP 0038626 A1 EP0038626 A1 EP 0038626A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
carboxylic acid
compound
process according
acid
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.)
Ceased
Application number
EP81301187A
Other languages
German (de)
English (en)
Inventor
David Alfred Hall
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 EP0038626A1 publication Critical patent/EP0038626A1/fr
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/25—Reduction

Definitions

  • the first reduction occurs at the point of the E-i curve between A and B.
  • Point A marks the initial onset of current flow of the first reduction
  • point B marks the initial onset of current flow of the second reduction.
  • Point C indicates the onset of background discharge, which is the point where the solvent- electrolyte system begins to break down in an uncontrolled electrolysis, discharging hydrogen.
  • the process of this invention is carried out in an acidic working fluid, which is made acid by the addition of an acid having a pK a of 0 or less, determined in water, preferably sulfuric acid or hydrochloric acid.
  • an acid having a pK a of 0 or less determined in water, preferably sulfuric acid or hydrochloric acid.
  • Other strong acids such as phosphoric acid, nitric acid, p-toluenesulfonic acid and the like may also be used.
  • Useful electrolytes for this purpose include, for-example, tetraethylammonium perchlorate, tetrabutylammonium perchlorate, benzotri- butylammonium chloride, benzyltriethylammonium bromide, benzyltriethylammonium chloride, methyltributylammonium iodide, tribenzylethylammonium p-toluenesulfonate, and the like electrolytes.
  • The- same organic electrolytes are used when the working fluid is non-aqueous, if the acid is immiscible with the solvent.
  • the working fluids were mixtures of dimethylformamide and hydrochloric acid.
  • Various amounts and concentrations of'hydrochloric acid were used in the various experiments, as detailed in the table below.
  • the cells and methods were as described in the text introducing Examples 1-29, except that in some experiments, the working and auxiliary electrodes were separated by a frit coated with a gel, as described in the introduction to Examples 30-40.
  • the table below indicates the experiments in which a gel-coated frit was used.
  • the working fluid used in this example was composed of 40 ml. of dimethylformamide and 10 ml. of pH 5.0 sodium acetate buffer, with sufficient p-toluenesulfonic acid added to the mixture to make it 1.8N.
  • the working electrode was a pool of mercury, and the counter electrode was a platinum wire, immersed in the working fluid with no electrode separation.
  • the reference electrode was saturated calomel.
  • the working electrode was mercury, and the auxiliary electrode was a platinum wire, separated from the working electrode by a fine glass frit coated with potassium sulfate-saturated agar.
  • the reference electrode was saturated calomel, with the porous junction placed as close as possible to the working electrode.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Cephalosporin Compounds (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
EP81301187A 1980-03-31 1981-03-19 Procédé de réduction électrolytique de céphalosporine p-nitrobenzyl-esters Ceased EP0038626A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13582980A 1980-03-31 1980-03-31
US135829 1980-03-31

Publications (1)

Publication Number Publication Date
EP0038626A1 true EP0038626A1 (fr) 1981-10-28

Family

ID=22469892

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81301187A Ceased EP0038626A1 (fr) 1980-03-31 1981-03-19 Procédé de réduction électrolytique de céphalosporine p-nitrobenzyl-esters

Country Status (7)

Country Link
EP (1) EP0038626A1 (fr)
JP (1) JPS56152982A (fr)
KR (1) KR830005237A (fr)
CA (1) CA1164402A (fr)
GB (1) GB2074607B (fr)
HU (1) HU185631B (fr)
IL (1) IL62427A (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3632850A (en) * 1969-03-18 1972-01-04 Lilly Co Eli Cephalexin synthesis
US4042472A (en) * 1976-04-12 1977-08-16 Eli Lilly And Company Electrolytic process for 7-methoxy-3-exomethylenecepham compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3632850A (en) * 1969-03-18 1972-01-04 Lilly Co Eli Cephalexin synthesis
US4042472A (en) * 1976-04-12 1977-08-16 Eli Lilly And Company Electrolytic process for 7-methoxy-3-exomethylenecepham compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Angew. Chem. Int. ED. Engl., Vol. 15 (1976), No. 5 V.G. MAIRANOVSKY: "Electro-Deprotection/Electrochemical Removal of Protecting Groups", pages 281-292 * paragraph 3.3., pages 285-286 table 2, page 290 * *
Techniques of Chemistry, Vol. V, Part II, Technique of Electro-Organic Synthesis, Edited by N.L. Weinberg Electrochemical Reduction of Nitrocompounds pages 137-140 John Wiley & Sons *

Also Published As

Publication number Publication date
JPS56152982A (en) 1981-11-26
HU185631B (en) 1985-03-28
CA1164402A (fr) 1984-03-27
GB2074607B (en) 1983-02-16
GB2074607A (en) 1981-11-04
IL62427A (en) 1984-07-31
KR830005237A (ko) 1983-08-03

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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17P Request for examination filed

Effective date: 19810324

AK Designated contracting states

Designated state(s): BE CH DE FR GB IT LU NL SE

STAA Information on the status of an ep patent application or granted ep patent

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Effective date: 19850106

RIN1 Information on inventor provided before grant (corrected)

Inventor name: HALL, DAVID ALFRED