GB960665A - Azidophenylacetic acid resolution - Google Patents

Azidophenylacetic acid resolution

Info

Publication number
GB960665A
GB960665A GB1014062A GB1014062A GB960665A GB 960665 A GB960665 A GB 960665A GB 1014062 A GB1014062 A GB 1014062A GB 1014062 A GB1014062 A GB 1014062A GB 960665 A GB960665 A GB 960665A
Authority
GB
United Kingdom
Prior art keywords
acid
azidophenylacetic
amino
optically active
penicillin
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
GB1014062A
Inventor
Berndt Olof Harald Sjoberg
Bertil Ake Ekstrom
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.)
Beecham Research Laboratories Ltd
Original Assignee
Beecham Research Laboratories 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 Beecham Research Laboratories Ltd filed Critical Beecham Research Laboratories Ltd
Priority to GB1014062A priority Critical patent/GB960665A/en
Priority to CH306363A priority patent/CH420105A/en
Publication of GB960665A publication Critical patent/GB960665A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • 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

Landscapes

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

Abstract

The invention comprises D(-) and L(+)-a -azidophenylacetic acids and salts thereof with one of the optically active bases 1-ephedrine, dehydrobietylamine, a -(2-naphthyl) ethylamine, cinchonidine, cinchonine, quinidine, quinine, brucine, strychnine or morphine. The optically active isomers may be obtained by treating DL-a -azidophenylacetic acid with one of the above bases in an organic solvent, separating the D(-) salt by fractional crystallisation and recovering the free acid therefrom, e.g. by treatment with an acid such as cold dilute hydrochloric acid. The L(+)-a -azido-phenylacetic acid remaining in the mother liquors may be recovered and racemised with dilute aqueous sodium hydroxide and the racemic acid then resolved. D(-)-a -amino-benzyl penicillin may be made by converting D(-)-a -azidophenylacetic acid to the chloride, e.g. with thionyl chloride in trichloroethylene, which is then coupled with 6-amino-penicillanic acid to give D(-)-a -azidobenzyl penicillin which is then reduced, for example by catalytic hydrogenation with Raney nickel.
GB1014062A 1962-03-16 1962-03-16 Azidophenylacetic acid resolution Expired GB960665A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB1014062A GB960665A (en) 1962-03-16 1962-03-16 Azidophenylacetic acid resolution
CH306363A CH420105A (en) 1962-03-16 1963-03-11 Process for the decomposition of DL-a-azido-phenylacetic acid into the optically active forms

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1014062A GB960665A (en) 1962-03-16 1962-03-16 Azidophenylacetic acid resolution

Publications (1)

Publication Number Publication Date
GB960665A true GB960665A (en) 1964-06-10

Family

ID=9962245

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1014062A Expired GB960665A (en) 1962-03-16 1962-03-16 Azidophenylacetic acid resolution

Country Status (2)

Country Link
CH (1) CH420105A (en)
GB (1) GB960665A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2127260A1 (en) * 1971-06-02 1972-12-14 Bayer Ag, 5090 Leverkusen Process for the preparation of D () alpha azidophenyl acetic acid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8300536A (en) * 1983-02-14 1984-09-03 Oce Andeno Bv OPTICALLY ACTIVE ALFA-AZIDO-P-HYDROXYPHENYLACACIC ACID AND ITS SALTS AND ITS PREPARATION.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2127260A1 (en) * 1971-06-02 1972-12-14 Bayer Ag, 5090 Leverkusen Process for the preparation of D () alpha azidophenyl acetic acid

Also Published As

Publication number Publication date
CH420105A (en) 1966-09-15

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