http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1243414-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/C07F9-65505 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D303-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-141 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-655 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D303-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-141 |
| filingDate | 1969-05-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_744b8d80e8cc1a5fd1662140d5706b8d http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_e2f5a51839c3b8e49a63696eac25fc0f |
| publicationDate | 1971-08-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1243414-A |
| titleOfInvention | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and derivatives thereof |
| abstract | 1,243,414. Preparing cis-1 ,2-epoxypropyl phosphonic acid and its esters and salts. MERCK & CO. Ltd. 12 May, 1969 [15 May, 1968], No. 23968/69. Heading C2C. A compound of the formula wherein R is an ester-forming group is obtained by reacting a phosphite ester P(OR) 3 with a compound of the formula wherein X is a halogen atom or a quaternary ammonium salt radical. The radical R may be alkyl, cycloalkyl, alkenyl, C 2 -C 5 alkynyl, cyano C 1 -C 5 alkyl, aryl, C 1 -C 5 alkyl substituted mononuclear aryl, or aralkyl, and X is halogen, e.g.Cl,Br or I or a quaternary ammonium salt radical, e.g. one having a cation of the formula <SP>+</SP>-NR<SP>1</SP>R<SP>2</SP>R<SP>3</SP> wherein R<SP>1</SP> is C 1 -C 5 alkyl and R<SP>2</SP> and R<SP>3</SP> are each C 1 -C 5 alkyl or R<SP>2</SP> and R<SP>3</SP> together with the N atom form a heterocyclic group, e.g. piperidino. The reaction is generally carried out in an inert solvent and the isomeric ester mixture formed can be separated, e.g. by gas- or adsorption chromatography, to yield the esters of () cis- and () trans - (1,2 - epoxypropyl) phosphonic acid. The esters of the () cis acid can be converted to the free acid or salts thereof, which have antibiotic properties, by various defined methods and the free acid can be converted to alkali metal-or alkaline earth metal salts or to the amine salts by treatment with an appropriate base. The 1,X-1,2-propylene oxide compounds of Formula I in which X is halogen may be obtained by treating a compound of the formula CH 3 CH = CHX with an oxidizing agent, e.g. perbenzoic acid, metachloroperbenzoic acid, trifluoroperacetic acid or perphthalic acid. The compounds I in which X is a quaternary ammonium salt radical are obtained by reacting an a-halopropionaldehyde with a secondary amine, e.g. piperidine, in the presence of a base and then reacting the product with a C 1 -C 5 alkyl iodide. Tricyanoethyl phosphite is obtained by reacting #-hydroxypropionitrile in benzene with PCl 3 in triethylamine at 10 C. Tri-tert butyl phosphite is obtained similarly using tertbutanol instead of the #-hydroxy propionitrile. |
| priorityDate | 1968-05-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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