http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1356582-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_73ee0bacab5a7576a6a3244747f6ea99 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C405-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D307-935 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D307-935 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C405-00 |
| filingDate | 1971-03-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1974-06-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1356582-A |
| titleOfInvention | Process for the manufacture of prostadienoic acid derivatives |
| abstract | 1356582 Prostaglandins; dimethyl 2-oxononylphosphonate IMPERIAL CHEMICAL INDUSTRIES Ltd 9 Feb 1972 [22 March 1971] 7469/71 Headings C2C and C2P The invention comprises a process for the manufacture of either C-15 epimer of 20-ethyl- 9α,11α,15 - trihydroxy - cis - 5, trans - 13- prostadienoic acid or an ester thereof with a C 1-6 alkanol which includes the crystallization of a mixture of the epimers of the p-phenylbenzoate ester of the Formula II containing 50% or more of one epimer to give a compound of Formula II enriched in that epimer and containing at least 75% of that epimer, a compound of Formula II above containing at least 75% of one epimer and a mixture of equal parts of the epimers of Formula II above, which is obtained by reducing 2,3,3α#, 6α# - tetrahydro - 2 - oxo - 4# - (3 - oxodec - trans- 1 - enyl) - 5α - (p - phenylbenzoyloxy)cyclopenteno- [b]furan resulting from the reaction between dimethyl 2-oxononylphosphonate, n-butyl lithium and 2,3,3α#,6α# - tetrahydro - 4# -formyl- 2 - oxo - 5α - (p - phenylbenzoyloxy)cyclopenteno- [b]furan, resulting from the oxidation of 2,3,3α#, 6a# - tetrahydro - 4# - hydroxymethyl - 2 - oxo- 5α - (p - phenylbenzoyloxy)cyclopenteno[b]furan, obtained by the demethylation of 2,3,3α#,6α#- tetrahydro - 4# - methoxymethyl - 2 - oxo - 5α - (pphenylbenzoyloxy)cyclopentenu[b]furan, which is prepared by diodinating 2,3,3α#,6α#-tetrahydro- 6# - iodo - 4# - methoxymethyl - 2 - oxo - 5α - (pphenylbenzoyloxy)cyclopenteno[b] furan, obtained by reacting p-phenylbenzoyl chloride with 5α- hydroxy - 6# - iodo - 4# - methoxymethyl - 2- oxo - 2,3,3α#,6α# - tetrahydrocyclopenteno[b]- furan. 20 - Ethyl - 9α,11α,15 - trihydroxy - cis - 5, trans-13-prostadienoic acid (90% of S-epimer) is prepared by hydrolysing the corresponding 11α,15-bis-(tetrahydropyranyl)ether, obtained by adding (4 - carboxybutyl)triphenylphosphonium bromide to a solution of 2,3,3α#,6α#-tetrahydro - 5α - (tetrahydropyran - 2 - yloxy) - 4# - [3S- (tetrahydropyran - 2 - yloxy) - dec - trans - 1- enyl] - 2# - hydroxycyclopenteno[b]furan, resulting from the reduction of the corresponding 2- oxocyclopenteno[b]furan derivative, which is prepared by reacting dihydropyran 2 with 2,3,3α#, 6α# - tetrahydro - 5α - hydroxy - 4# - (3S - hydroxydec - trans - 1 - enyl) - 2 - oxocyclopenteno[b]furan, resulting from the hydrolysis of the 3S-epimer of the compound of Formula II above. Dimethyl 2-oxononylphosphonate is prepared by reacting dimethyl methylphosphonate with nbutyl lithium and ethyl octanoate. |
| priorityDate | 1971-03-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 32.