GB1008468A - N-substituted 6-amino penicillanic acids - Google Patents

N-substituted 6-amino penicillanic acids

Info

Publication number
GB1008468A
GB1008468A GB1104562A GB1104562A GB1008468A GB 1008468 A GB1008468 A GB 1008468A GB 1104562 A GB1104562 A GB 1104562A GB 1104562 A GB1104562 A GB 1104562A GB 1008468 A GB1008468 A GB 1008468A
Authority
GB
United Kingdom
Prior art keywords
acid
aminopenicillanic
hydrogen
group
product
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
GB1104562A
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.)
Gruenenthal GmbH
Original Assignee
Gruenenthal GmbH
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 Gruenenthal GmbH filed Critical Gruenenthal GmbH
Publication of GB1008468A publication Critical patent/GB1008468A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Abstract

N - substituted 6 - aminopenicillanic acids are prepared by reacting 6-aminopenicillanic acid with silylating agents of general formula <FORM:1008468/C3/1> wherein R1,R2 and R3 which may be the same or different are alkyl or aryl groups and X is hydrogen, halogen, the group -NH-Si­(R1)(R2)(R3) or the group -N=(R4)(R5) wherein R4 and R5\t which may be the same or different are hydrogen or alkyl groups. Preferably the reaction takes place in a non-proton active non-polar solvent and, in the absence of a proton active compound, at temperatures between room temperature and the boiling point of the silylating agent. Specified silylating agents are trialkylchlorosilanes, used in the presence of ammonia, and trialkylsilanes which are used in the presence of a catalyst, e.g. palladium or H2PtCl6. The examples describe the reaction of 6-aminopenicillanic acid with an excess of hexamethyldisilazane to give N-trimethylsilyl-6-aminopenicillanic acid trimethylsilyl ester.ALSO:Derivatives of 6-aminopenicillanic acid are prepared by reacting 6-aminopenicillanic acid with silylating agents of general formula <FORM:1008468/C2/1> wherein R1, R2 and R3 which may be the sam or different are alkyl or aryl groups and X is hydrogen; the group -NH-Si(R1)(R2)(R3) or the group -N(R4)(R5), wherein R4 and R5, which may be the same or different are hydrogen or alkyl groups, dissolving the product in excess of the silylating agent or in a non-polar solvent, acylating the silylated product and then removing the silicon containing groups by hydrolysis. Specified acylating agents are acid halides, acid anhydrides, ketenes, iso-cyanates and isothiocyanates. Acylation can take place in excess of the silylating agent without isolating the silylated 6-aminopenicillanic acid. Preferably an acid chloride is used in presence of a compound capable of fixing hydrogen chloride. In the examples, a solution of N-trimethylsilyl-6-aminopenicillanic acid trimethylsilyl ester in hexamethyldisilazane is reacted with (1) phenylacetic acid chloride in the presence of triethylamine at room temperature to 40 DEG C.; hydrolysis of the product with water giving penicillin G; and (2) truxillic acid chloride in the presence of triethylamine. The product was converted into truxillic acid-di-penicillin by exposure to the moisture in the air.
GB1104562A 1961-03-23 1962-03-22 N-substituted 6-amino penicillanic acids Expired GB1008468A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0061834 1961-03-23

Publications (1)

Publication Number Publication Date
GB1008468A true GB1008468A (en) 1965-10-27

Family

ID=6973349

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1104562A Expired GB1008468A (en) 1961-03-23 1962-03-22 N-substituted 6-amino penicillanic acids

Country Status (5)

Country Link
CH (1) CH423782A (en)
DE (1) DE1420981C3 (en)
DK (1) DK130590B (en)
GB (1) GB1008468A (en)
SE (1) SE372535B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182709A (en) * 1976-01-15 1980-01-08 Glaxo Group Limited Manufacture of semi-synthetic penicillin antibiotics
US4240960A (en) * 1979-03-19 1980-12-23 Bristol-Myers Company Trimethylsilyl substituted penicillins
US4278600A (en) 1979-03-19 1981-07-14 Bristol-Myers Company Production of penicillins
US4310458A (en) 1979-03-19 1982-01-12 Bristol-Myers Company Production of penicillins
US4351766A (en) * 1979-07-12 1982-09-28 Bristol-Myers Company Production of penicillins
US7230097B2 (en) 2003-03-10 2007-06-12 Lupin Ltd. Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182709A (en) * 1976-01-15 1980-01-08 Glaxo Group Limited Manufacture of semi-synthetic penicillin antibiotics
US4240960A (en) * 1979-03-19 1980-12-23 Bristol-Myers Company Trimethylsilyl substituted penicillins
US4278600A (en) 1979-03-19 1981-07-14 Bristol-Myers Company Production of penicillins
US4310458A (en) 1979-03-19 1982-01-12 Bristol-Myers Company Production of penicillins
US4351766A (en) * 1979-07-12 1982-09-28 Bristol-Myers Company Production of penicillins
US7230097B2 (en) 2003-03-10 2007-06-12 Lupin Ltd. Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid
US7427692B2 (en) 2003-03-10 2008-09-23 Lupin Ltd. Process for preparation of 7-[α-amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid

Also Published As

Publication number Publication date
DK130590C (en) 1975-08-11
CH423782A (en) 1966-11-15
DK130590B (en) 1975-03-10
DE1420981B2 (en) 1975-05-15
DE1420981C3 (en) 1976-01-02
SE372535B (en) 1974-12-23
DE1420981A1 (en) 1969-05-29

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