GB630712A - Process of preparing intermediates useful in the preparation of penicill amine - Google Patents

Process of preparing intermediates useful in the preparation of penicill amine

Info

Publication number
GB630712A
GB630712A GB7002/47A GB700247A GB630712A GB 630712 A GB630712 A GB 630712A GB 7002/47 A GB7002/47 A GB 7002/47A GB 700247 A GB700247 A GB 700247A GB 630712 A GB630712 A GB 630712A
Authority
GB
United Kingdom
Prior art keywords
valine
reaction mixture
oxazolone
treating
haloacyl
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
GB7002/47A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB630712A publication Critical patent/GB630712A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or 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
    • C07D263/36—One oxygen atom
    • C07D263/42—One oxygen atom attached in position 5

Landscapes

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

Abstract

Addition compounds or salts are formed by treating an N-a -haloacyl valine with a nitrogen heterocyclic compound having a pyridine nucleus. Treatment of the product with acetic anhydride gives a 2-alkyl-4-isopropylidene-5-oxazolone which may be treated with water, e.g. by adding the reaction mixture to water, to form an a -acylamino-b : b -dimethylacrylic acid. If the reaction mixture is added to anhy drous alcohol such as benzyl alcohol, methyl alcohol or ethyl alcohol, the corresponding ester is formed instead of the free acid. Reaction of the oxazolone or dimethylacrylic acid products with hydrogen sulphide followed by hydrolysis gives dl-penicillamine. The N-a -haloacyl valine is prepared by treating valine with an a -haloacyl halide in aqueous alkali. In examples (1) N-chloroacetyl valine prepared by treating dl-valine in aqueous sodium hydroxide with chloroacetyl chloride is reacted with pyridine to form a crystalline compound. this product is heated with acetic anhydride and the reaction mixture is poured into water giving a -acetylamino-b : b -dimethylacrylic acid; (2) the reaction mixture obtained as in (1) is distilled in vacuo to give 2-methyl-4-isopropylide-5-oxazolone.
GB7002/47A 1946-03-22 1947-03-13 Process of preparing intermediates useful in the preparation of penicill amine Expired GB630712A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US630712XA 1946-03-22 1946-03-22

Publications (1)

Publication Number Publication Date
GB630712A true GB630712A (en) 1949-10-19

Family

ID=22046722

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7002/47A Expired GB630712A (en) 1946-03-22 1947-03-13 Process of preparing intermediates useful in the preparation of penicill amine

Country Status (1)

Country Link
GB (1) GB630712A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1814854A1 (en) * 2004-10-29 2007-08-08 MUSC Foundation For Research Development Cationic ceramides, and analogs thereof, and their use for preventing or treating cancer
US8592419B2 (en) 2004-10-29 2013-11-26 Musc Foundation For Research Development Ceramides and apoptosis-signaling ligand
US8697379B2 (en) 2008-11-06 2014-04-15 Musc Foundation For Research Development Lysosomotropic inhibitors of acid ceramidase

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1814854A1 (en) * 2004-10-29 2007-08-08 MUSC Foundation For Research Development Cationic ceramides, and analogs thereof, and their use for preventing or treating cancer
EP1814854A4 (en) * 2004-10-29 2009-08-05 Musc Found For Res Dev Cationic ceramides, and analogs thereof, and their use for preventing or treating cancer
US8093393B2 (en) 2004-10-29 2012-01-10 Musc Foundation For Research Development Cationic ceramides, and analogs thereof, and their use for preventing or treating cancer
US8592419B2 (en) 2004-10-29 2013-11-26 Musc Foundation For Research Development Ceramides and apoptosis-signaling ligand
US8697379B2 (en) 2008-11-06 2014-04-15 Musc Foundation For Research Development Lysosomotropic inhibitors of acid ceramidase

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