JPS57139077A - Eliminating method of protecting group from carboxy group - Google Patents

Eliminating method of protecting group from carboxy group

Info

Publication number
JPS57139077A
JPS57139077A JP56025059A JP2505981A JPS57139077A JP S57139077 A JPS57139077 A JP S57139077A JP 56025059 A JP56025059 A JP 56025059A JP 2505981 A JP2505981 A JP 2505981A JP S57139077 A JPS57139077 A JP S57139077A
Authority
JP
Japan
Prior art keywords
zinc
group
mineral
compound
sulfonic 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.)
Granted
Application number
JP56025059A
Other languages
Japanese (ja)
Other versions
JPH0310626B2 (en
Inventor
Junichi Nakazawa
Masanao Kaneko
Takeo Miyaoka
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.)
Sankyo Co Ltd
Original Assignee
Sankyo Co Ltd
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 Sankyo Co Ltd filed Critical Sankyo Co Ltd
Priority to JP56025059A priority Critical patent/JPS57139077A/en
Priority to SE8201087A priority patent/SE452620B/en
Priority to CH108282A priority patent/CH646977A5/en
Priority to DK075582A priority patent/DK162603C/en
Priority to ES509837A priority patent/ES8305362A1/en
Priority to FI820582A priority patent/FI72521C/en
Priority to CA000396796A priority patent/CA1194470A/en
Priority to IT67194/82A priority patent/IT1157951B/en
Priority to NL8200708A priority patent/NL8200708A/en
Publication of JPS57139077A publication Critical patent/JPS57139077A/en
Publication of JPH0310626B2 publication Critical patent/JPH0310626B2/ja
Granted 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
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/36—Methylene radicals, substituted by sulfur atoms
    • 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
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

PURPOSE:To obtain a cephalosporin derivative useful as a medicine advantageously, by eliminating only the phenacyl ester part at the 4-position with a mineral or sulfonic acid and zinc in an inert solvent without converting the heterocyclic ring thiomethyl group at the 3-position. CONSTITUTION:A compound of formulaI(R<1> is H or acyl; R<2> is H or methoxyl; R<3> is formula II or S-heterocyclic ring; R<4> is H or halogen; X is S, O or methylene), e.g. phenacyl 7beta-cyanomethylthioacetamido-7alpha-methoxy-3-(1-methyl-1H- tetrazol-5-yl)tiomethyl-3-cephem-4-carboxylate, is reacted with zinc and a mineral or sulfonic acid in an inert solvent, preferably hydrous acetone, to give a compound of formula III. The amount of the zinc to be used is 1-2 times that of the raw ester. The reaction temperature is -50-+5 deg.C, preferably -30-+20 deg.C.
JP56025059A 1981-02-23 1981-02-23 Eliminating method of protecting group from carboxy group Granted JPS57139077A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
JP56025059A JPS57139077A (en) 1981-02-23 1981-02-23 Eliminating method of protecting group from carboxy group
SE8201087A SE452620B (en) 1981-02-23 1982-02-22 PROCEDURE FOR THE PREPARATION OF BETA-LACTIC ANTIBIOTICS DERIVATIVES
CH108282A CH646977A5 (en) 1981-02-23 1982-02-22 Process for the preparation of derivatives of beta-lactam antibiotics
DK075582A DK162603C (en) 1981-02-23 1982-02-22 PROCEDURE FOR PREPARING BETA-LACTAM ANTIBIOTICA
ES509837A ES8305362A1 (en) 1981-02-23 1982-02-23 A procedure for preparing derivatives of antibioticos-lactamicos. (Machine-translation by Google Translate, not legally binding)
FI820582A FI72521C (en) 1981-02-23 1982-02-23 Process for the preparation of cephalosporin derivatives.
CA000396796A CA1194470A (en) 1981-02-23 1982-02-23 PROCESS FOR PREPARING DERIVATIVES OF .beta.-LACTAM ANTI- BIOTICS
IT67194/82A IT1157951B (en) 1981-02-23 1982-02-23 PROCEDURE FOR THE PREPARATION OF BETALACTAMIC ANTIBIOTICS
NL8200708A NL8200708A (en) 1981-02-23 1982-02-23 PROCESS FOR THE PREPARATION OF BETA-LACTAMANTIBIOTIC COMPOUNDS.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP56025059A JPS57139077A (en) 1981-02-23 1981-02-23 Eliminating method of protecting group from carboxy group

Publications (2)

Publication Number Publication Date
JPS57139077A true JPS57139077A (en) 1982-08-27
JPH0310626B2 JPH0310626B2 (en) 1991-02-14

Family

ID=12155348

Family Applications (1)

Application Number Title Priority Date Filing Date
JP56025059A Granted JPS57139077A (en) 1981-02-23 1981-02-23 Eliminating method of protecting group from carboxy group

Country Status (1)

Country Link
JP (1) JPS57139077A (en)

Also Published As

Publication number Publication date
JPH0310626B2 (en) 1991-02-14

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