http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-812830-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D417-12 |
| filingDate | 1955-12-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1959-05-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-812830-A |
| titleOfInvention | Aminoisoxazolidone compounds |
| abstract | The invention comprises compounds of the formula <FORM:0812830/IV (b)/1> in which X, Y and Z are H or alkyl, aralkyl or aryl of 1-8 carbon atoms, and R and R2 are H or alkyl or aralkyl of 1-8 carbon atoms. These are made by treating with a base compounds of the formula R-NH-O-CXY-CZ (NHR2)-COOR4 or acid addition salts thereof, where R4 is C1-C8 alkyl. The base used for cyclisation is preferably an aqueous alkali metal hydroxide in amount and concentration such that the pH after the reaction is 10-11. The mixture is preferably left to stand for 10-30 minutes and then acidified with an acid (e.g. hydrochloric or acetic), if desired after addition of an ethanol-isopropanol mixture and removal of inorganic salts. The product then crystallizes or is adsorbed on an anion-exchange resin and thence removed with water in the presence of carbon dioxide. Examples show the preparation of 4-amino-3-isoxazolidone and its 5-methyl derivative, the former being resolved with tartaric acid. Starting materials are mentioned in which R and R2 are also methyl, propyl and benzyl, X and Y are methyl, ethyl or phenyl and Z is methyl or benzyl. The products are anti-bacterial agents for animals and plants. The starting materials are prepared as follows: a 4-carbalkoxy-oxazoline of the formula <FORM:0812830/IV (b)/2> where R3 is C1-C8 alkyl, aryl or aralkyl and R5 is C1-C8 alkyl, is treated with an hydroxylamine R-NHOH in the presence of a base under anhydrous conditions to give an hydroxylamide <FORM:0812830/IV (b)/3> and the latter reacted with R2Q in an inert solvent to form <FORM:0812830/IV (b)/4> where Q is chlorine, bromine or iodine. Alkaline cyclisation in a water-miscible solvent produces a 4-acylamino-isoxazolidone, <FORM:0812830/IV (b)/5> which when treated with R4OH under acidic conditions forms the required compound R-NH -O-CXY-CZ(NHR2)-COOR4. Typical compounds and reagents are specified for each step. Examples are given of the preparation of 2 - phenyl - 4 - carbohydroxamido - 2 - oxazoline, 2 - phenyl - 4 - carbohydroxamide - 5-methyl - 2 - oxazoline, a - benzamido - b - chloropropionyl - hydroxylamine, a - benzamido - b -chloro - butyryl - hydroxylamine, 4 - benzamido - 3 - isoxazolidone, 4 - benzamido - 5-methyl - 3 - isoxazolidone, and methyl a -amino - b - aminoxy - propionate and butyrate as dihydrochlorides. 2 - Phenyl - 4 - carbohydroxamido - 2 - oxazoline is made by esterifying serine with ethanol in the presence of dry hydrogen chloride and reacting the resulting ester hydrochloride with benzimido ethyl ether (from benzonitrile, ethanol and dry hydrogen chloride). |
| priorityDate | 1954-12-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 55.