GB1155028A - Reactive Esters of Hydroxy-Thiazolidine Compounds and process for their manufacture - Google Patents

Reactive Esters of Hydroxy-Thiazolidine Compounds and process for their manufacture

Info

Publication number
GB1155028A
GB1155028A GB2438968A GB2438968A GB1155028A GB 1155028 A GB1155028 A GB 1155028A GB 2438968 A GB2438968 A GB 2438968A GB 2438968 A GB2438968 A GB 2438968A GB 1155028 A GB1155028 A GB 1155028A
Authority
GB
United Kingdom
Prior art keywords
acid
group
free
hydroxyl group
esterified
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
GB2438968A
Inventor
Robert Burns Woodward
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.)
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
Priority claimed from CH1262365A external-priority patent/CH480355A/en
Priority claimed from CH1697865A external-priority patent/CH497457A/en
Priority claimed from CH1698065A external-priority patent/CH497379A/en
Priority claimed from CH1697465A external-priority patent/CH497451A/en
Priority claimed from CH1697665A external-priority patent/CH497371A/en
Priority claimed from CH1697565A external-priority patent/CH497456A/en
Priority claimed from CH1696965A external-priority patent/CH497446A/en
Priority claimed from CH1698165A external-priority patent/CH497461A/en
Priority claimed from CH1697065A external-priority patent/CH497445A/en
Priority claimed from CH1697765A external-priority patent/CH497369A/en
Priority claimed from CH1697265A external-priority patent/CH497447A/en
Priority claimed from CH1697365A external-priority patent/CH497448A/en
Priority claimed from CH1697965A external-priority patent/CH497460A/en
Application filed by Individual filed Critical Individual
Priority claimed from GB38573/66A external-priority patent/GB1155020A/en
Publication of GB1155028A publication Critical patent/GB1155028A/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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/12—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing more than one —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,155,028. Thiazolidinyl-ester derivatives and process for their preparation. R. B. WOODWARD. 30 Aug., 1966 [10 Sept., 1965; 9 Dec., 1965; 3 Feb., 1966], No. 24389/68. Divided out of 1,155,020. Heading C2C. Compounds of the formula in which Ac represents an acyl group, X represents the disubstituted carbon atom of the thiazolidine ring, R 1 stands for a free or functionally converted carboxyl group and Y stands for a reactive, esterified hydroxyl group, the compounds wherein Y stands for a hydroxyl group esterified with a strong organic sulphonic acid, a hydrohalic acid or sulphuric acid being claimed as novel, may be obtained by reacting a 2,2-disubstituted-3-acyl-5-hydroxy-thiazolidine-4-carboxylic acid derivative of the formula with an acid or a functional derivative of an acid. The esterified hydroxyl group Y is a hydroxyl group esterified with an inorganic acid, e.g. a hydrohalic acid or sulphuric acid, or with a strong organic acid, e.g. an organic carboxylic acid or an organic sulphonic acid, and the esterifying group may be introduced by treating the hydroxy-starting material with, for example, an acid halide, an acid anhydride or a free acid. The above reaction may be effected in the presence or absence of a diluent, optionally in the presence of condensing agents and/or catalysts in a closed vessel and/or in an inert atmosphere. A resulting mixture of isomers may be resolved by conventional methods, e.g. fractional crystallization or distillation, adsorption chromatography; resulting racemates may be resolved by forming a mixture of diastereoisomeric salts with optically active salt-forming agents, separating the mixture into the diastereoisomeric salts and converting the isolated salts into the free compounds. In specific examples the only examples of the radicals Ac and X which are described are the t-butyloxycarbonyl radical and a dimethyl-substituted carbon atom respectively. The products of the invention may be chemically modified by conventional methods, for example an ester group R 1 may be converted to the free acid, or a free acid group R 1 may be converted to a functional derivative, many of which are described, e.g. ester, amide, azide, hydrazide, nitrile, azocarbonyl or azidocarbonyl.
GB2438968A 1965-09-10 1966-08-30 Reactive Esters of Hydroxy-Thiazolidine Compounds and process for their manufacture Expired GB1155028A (en)

Applications Claiming Priority (22)

Application Number Priority Date Filing Date Title
CH1262365A CH480355A (en) 1965-09-10 1965-09-10 Process for the preparation of 3-tert-butyloxycarbonyl-thiazolidine-4-carboxylic acids
CH1697465A CH497451A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1697665A CH497371A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1697765A CH497369A (en) 1965-12-09 1965-12-09 Alpha-diacylmethyl-alpha-hydroxymethane carboxylic acid esters - intermediates in the synthesis of cephalosporanic acids
CH1696965A CH497446A (en) 1965-12-09 1965-12-09 2 2-disubst-3-acyl-5-hydrazino-thiazolidine-4-carboxylic acid derivs
CH1698065A CH497379A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1697865A CH497457A (en) 1965-12-09 1965-12-09 Process for the prepn. of cpds. where ac = acyl; X = disubstd. C atom; Ra= an alcohol residue; Ro= H or an acyl. Intermediates in the prepn. of phar
CH1697565A CH497456A (en) 1965-12-09 1965-12-09 Azetidine compounds and process for their manufacture
CH1697265A CH497447A (en) 1965-12-09 1965-12-09 (3)-Acyl-(5)-acyloxy-thiazolidine-(4)-carboxylic acid derivs.
CH1697365A CH497448A (en) 1965-12-09 1965-12-09 Actinomyces aureofaciens ls-b-22-ol
CH1697965A CH497460A (en) 1965-12-09 1965-12-09 Process for the prepn. of cpds. where ac = acyl; X = disubstd. C atom; Ra= an alcohol residue; Ro= H or an acyl. Intermediates in the prepn. of phar
CH1697065A CH497445A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1698165A CH497461A (en) 1965-12-09 1965-12-09 Process for the preparation of 7-amino-deacetylcephalosporanic acid compounds
CH44866 1966-01-13
CH44666 1966-01-13
CH45166 1966-01-13
CH44966 1966-01-13
CH44766 1966-01-13
CH45066 1966-01-13
CH153066 1966-02-03
CH152966 1966-02-03
GB38573/66A GB1155020A (en) 1965-09-10 1966-08-30 Azido-Thiazolidine Compounds and process for their manufacture

Publications (1)

Publication Number Publication Date
GB1155028A true GB1155028A (en) 1969-06-11

Family

ID=27586562

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2438868A Expired GB1155027A (en) 1965-09-10 1966-08-30 Amino-Thiazolidine Compounds and process for their manufacture
GB2438968A Expired GB1155028A (en) 1965-09-10 1966-08-30 Reactive Esters of Hydroxy-Thiazolidine Compounds and process for their manufacture

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB2438868A Expired GB1155027A (en) 1965-09-10 1966-08-30 Amino-Thiazolidine Compounds and process for their manufacture

Country Status (1)

Country Link
GB (2) GB1155027A (en)

Also Published As

Publication number Publication date
GB1155027A (en) 1969-06-11

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