GB799066A - Process for the manufacture of isoxazolidone compounds - Google Patents

Process for the manufacture of isoxazolidone compounds

Info

Publication number
GB799066A
GB799066A GB35106/56A GB3510656A GB799066A GB 799066 A GB799066 A GB 799066A GB 35106/56 A GB35106/56 A GB 35106/56A GB 3510656 A GB3510656 A GB 3510656A GB 799066 A GB799066 A GB 799066A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
treated
hydroxylamine
give
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
GB35106/56A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB799066A publication Critical patent/GB799066A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises DL-threo-5-methyl-4 - aminoisoxazolidone - (3) and also a process for the preparation of 4-aminoisoxazolidone-(3) and its 5-alkyl derivatives by condensing a b -substituted a -aminopropionic acid of the general formula: <FORM:0799066/IV (b)/1> wherein R is a hydrogen atom or an alkyl group and A is the anion of an hydrohalic acid or a strong organic acid, with phosgene, preferably in an organic solvent, treating the resulting cyclic anhydride with hydroxylamine or a salt thereof to form a b -substituted a -aminopropiohydroxamic acid and cyclizing the latter in the presence of a basic agent. The reaction with hydroxylamine is preferably carried out using 2 to 4 mols. of hydroxylamine for each mol. of cyclic anhydride, at least one of the reaction components being in solution in a solvent such as water, methanol, ethanol, propanol, ether, dioxane and tetrahydrofurane. The final cyclization reaction is preferably carried out at a temperature not exceeding 70 DEG C. in the presence of a basic agent which may suitably be an alkali-metal alkoxide, an organic base or a basic ion-exchange resin. In examples: (1) a -amino-b -chloropropionic acid is treated with phosgene to give a cyclic anhydride, this product is treated with hydroxylamine in ethanol to form a -amino-b -chloro propiohydroxamic acid and this is treated with aqueous lithium hydroxide to give 4 - amino - isoxazolidone - (3), which is isolated by freeze-drying, extracting with ethanol and recrystallization; (2) a -amino-b -chloropropiohydroxamic acid, made as in (1), is treated with sodium ethoxide in ethanol to give 4-aminoisoxazolidone; (3), (4) and (5) a -amino-b -chloropropiohydroxamic acid, made as in (1), is converted to 4-aminoisoxazolidone by treatment with triethylamine; and (6) DL-allo-a -amino - b - chloro - butyric acid is treated with phosgene to give the cyclic anhydride DL-allo-4 - (a - chloroethyl) - 2 : 5 - dioxo - oxazolidine, this is treated with hydroxylamine to give DL-allo - a - amino - b - chlorobutyrohydroxamic acid and this product is cyclized in the presence of triethylamine to DL-threo 5-methyl-4-amino-isoxazolidone-(3).
GB35106/56A 1955-11-17 1956-11-16 Process for the manufacture of isoxazolidone compounds Expired GB799066A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH799066X 1955-11-17

Publications (1)

Publication Number Publication Date
GB799066A true GB799066A (en) 1958-07-30

Family

ID=4537506

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35106/56A Expired GB799066A (en) 1955-11-17 1956-11-16 Process for the manufacture of isoxazolidone compounds

Country Status (1)

Country Link
GB (1) GB799066A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017518272A (en) * 2014-04-30 2017-07-06 シンジェンタ パーティシペーションズ アーゲー Process for the preparation of substituted cycloserine
CN114163393A (en) * 2020-09-10 2022-03-11 浙江海正药业股份有限公司 Cycloserine crystal form and preparation method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017518272A (en) * 2014-04-30 2017-07-06 シンジェンタ パーティシペーションズ アーゲー Process for the preparation of substituted cycloserine
CN114163393A (en) * 2020-09-10 2022-03-11 浙江海正药业股份有限公司 Cycloserine crystal form and preparation method thereof
WO2022052969A1 (en) * 2020-09-10 2022-03-17 浙江海正药业股份有限公司 Cycloserine crystal form and preparation method therefor

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