GB1119806A - Process for the manufacture of 7-amino-cephalosporanic acid - Google Patents

Process for the manufacture of 7-amino-cephalosporanic acid

Info

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
Application number
GB4310765A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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
Priority claimed from CH199263A external-priority patent/CH433316A/en
Priority claimed from CH267563A external-priority patent/CH504471A/en
Priority claimed from DK72864A external-priority patent/DK118506B/en
Priority claimed from CH1316664A external-priority patent/CH467803A/en
Priority claimed from DK516765A external-priority patent/DK141847B/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1119806A publication Critical patent/GB1119806A/en
Expired legal-status Critical Current

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
    • 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.
GB4310765A 1963-02-18 1965-10-11 Process for the manufacture of 7-amino-cephalosporanic acid Expired GB1119806A (en)

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4562253A (en) * 1982-08-06 1985-12-31 Biochemie Gesellschaft M.B.H. Deacylation of amides

Cited By (1)

* Cited by examiner, † Cited by third party
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
NL6513095A (en) 1966-04-12
NL148610B (en) 1976-02-16

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