GB815525A - Production of tetracyclines - Google Patents

Production of tetracyclines

Info

Publication number
GB815525A
GB815525A GB29719/57A GB2971957A GB815525A GB 815525 A GB815525 A GB 815525A GB 29719/57 A GB29719/57 A GB 29719/57A GB 2971957 A GB2971957 A GB 2971957A GB 815525 A GB815525 A GB 815525A
Authority
GB
United Kingdom
Prior art keywords
tetracycline
epi
acid
solution
salt
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
GB29719/57A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid 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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB815525A publication Critical patent/GB815525A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A tetracycline is produced by preparing a solution of a 4 epi-tetracycline having the general formula <FORM:0815525/IV (b)/1> in which R1 is a hydrogen, chlorine or bromine atom and R2 is a hydrogen atom or a hydroxyl group, at least one of R1 and R2 being a hydrogen atom, or a salt with an acid or a base of such epi-tetracycline, adjusting the pH of the solution to within the range 3.0 to 5.0 and allowing the solution to stand until a substantial proportion of the epi-tetracycline is isomerized to the corresponding tetracycline and, if desired, reacting the tetracycline with an acid or a base to produce a salt thereof. The preferred solvent is an oxygenated, polar organic solvent such as methanol, ethanol, butanol, acetone, 2-ethoxy ethanol, 2-methoxy propanol, glacial acetic acid, tetrahydrofuran, dimethylformamide and mixtures thereof. The preferred pH is 3.5 to 4.5 maintained by the use of buffers such as sodium dihydrogen phosphate. Isomerization may be carried out at room temperatures and may require 24 hours at 25 DEG C. The tetracyclines may be recovered from the solutions so produced by (a) fractional crystallization, (b) countercurrent extraction, (c) chromatographic adsorption, or (d) partition chromatography. In the example, an aqueous solution of ammonium 4-epi-tetracycline was adjusted to pH 4.25 with formic acid and allowed to stand overnight. The precipitate was removed, washed with water, treated with hydrochloric acid to form the hydrochloride and recrystallized from 2-ethoxyethanol.
GB29719/57A 1954-10-22 1955-10-18 Production of tetracyclines Expired GB815525A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US815525XA 1954-10-22 1954-10-22

Publications (1)

Publication Number Publication Date
GB815525A true GB815525A (en) 1959-06-24

Family

ID=22164893

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29719/57A Expired GB815525A (en) 1954-10-22 1955-10-18 Production of tetracyclines

Country Status (1)

Country Link
GB (1) GB815525A (en)

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