FR2220531A1 - Synthesis of penicillins from 6-amino penicillanic acid - by acylation with acid chlorides using hexamethylphosphotriamide as solvent - Google Patents

Synthesis of penicillins from 6-amino penicillanic acid - by acylation with acid chlorides using hexamethylphosphotriamide as solvent

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Publication number
FR2220531A1
FR2220531A1 FR7307848A FR7307848A FR2220531A1 FR 2220531 A1 FR2220531 A1 FR 2220531A1 FR 7307848 A FR7307848 A FR 7307848A FR 7307848 A FR7307848 A FR 7307848A FR 2220531 A1 FR2220531 A1 FR 2220531A1
Authority
FR
France
Prior art keywords
hexamethylphosphotriamide
penicillins
acid
solvent
acylation
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
FR7307848A
Other languages
French (fr)
Other versions
FR2220531B1 (en
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Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to FR7307848A priority Critical patent/FR2220531A1/en
Publication of FR2220531A1 publication Critical patent/FR2220531A1/en
Application granted granted Critical
Publication of FR2220531B1 publication Critical patent/FR2220531B1/fr
Granted legal-status Critical Current

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Classifications

    • 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
    • C07D499/04—Preparation
    • C07D499/10—Modification of an amino radical directly attached in position 6
    • C07D499/12—Acylation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Penicillins of formula (I):-(where Z is an opt. mono-or polysubstd. alicyclic, aromatic or heterocyclic gp.) are prepd. by (a) reacting ZCOOH with a chlorinating agent (esp. POCI3 and/or PCI5) in hexamethylphosphotriamide (HMPT) to form ZCOC1 and (b) reacting the ZCOC1 with 6-aminopenicillanic acid in HMPT. The use of HMPT as solvent increases the yield and gives high-purity (I) without the need for additional purification.
FR7307848A 1973-03-06 1973-03-06 Synthesis of penicillins from 6-amino penicillanic acid - by acylation with acid chlorides using hexamethylphosphotriamide as solvent Granted FR2220531A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7307848A FR2220531A1 (en) 1973-03-06 1973-03-06 Synthesis of penicillins from 6-amino penicillanic acid - by acylation with acid chlorides using hexamethylphosphotriamide as solvent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7307848A FR2220531A1 (en) 1973-03-06 1973-03-06 Synthesis of penicillins from 6-amino penicillanic acid - by acylation with acid chlorides using hexamethylphosphotriamide as solvent

Publications (2)

Publication Number Publication Date
FR2220531A1 true FR2220531A1 (en) 1974-10-04
FR2220531B1 FR2220531B1 (en) 1976-11-05

Family

ID=9115818

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7307848A Granted FR2220531A1 (en) 1973-03-06 1973-03-06 Synthesis of penicillins from 6-amino penicillanic acid - by acylation with acid chlorides using hexamethylphosphotriamide as solvent

Country Status (1)

Country Link
FR (1) FR2220531A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2338278A1 (en) * 1976-01-15 1977-08-12 Glaxo Lab Ltd IMPROVEMENTS IN THE MANUFACTURING OF ANTIBIOTICS OF THE PENICILLIN TYPE, SEMI-SYNTHETICS
EP0439096A2 (en) * 1990-01-22 1991-07-31 Biochemie Gesellschaft M.B.H. Improvements in or relating to beta lactam production
CN102964356A (en) * 2012-12-25 2013-03-13 菏泽睿智科技开发有限公司 Synthesis method of flucloxacillin sodium

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2013456A1 (en) * 1968-07-22 1970-04-03 Erasme Mixed anhydrides of carboxylic and phos - phorous or phosphoric acids useful as

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2013456A1 (en) * 1968-07-22 1970-04-03 Erasme Mixed anhydrides of carboxylic and phos - phorous or phosphoric acids useful as

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2338278A1 (en) * 1976-01-15 1977-08-12 Glaxo Lab Ltd IMPROVEMENTS IN THE MANUFACTURING OF ANTIBIOTICS OF THE PENICILLIN TYPE, SEMI-SYNTHETICS
EP0439096A2 (en) * 1990-01-22 1991-07-31 Biochemie Gesellschaft M.B.H. Improvements in or relating to beta lactam production
EP0439096A3 (en) * 1990-01-22 1992-06-10 Biochemie Gesellschaft M.B.H. Improvements in or relating to beta lactam production
EP0976755A1 (en) * 1990-01-22 2000-02-02 BIOCHEMIE Gesellschaft m.b.H. Improvements in or relating to beta lactam production
CN102964356A (en) * 2012-12-25 2013-03-13 菏泽睿智科技开发有限公司 Synthesis method of flucloxacillin sodium
CN102964356B (en) * 2012-12-25 2015-06-17 菏泽睿智科技开发有限公司 Synthesis method of flucloxacillin sodium

Also Published As

Publication number Publication date
FR2220531B1 (en) 1976-11-05

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