http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1513211-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_7b4beef0c137d9094e6918ee382be22f |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-0053 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J71-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J7-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C12P33-16 |
| filingDate | 1976-01-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1978-06-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1513211-A |
| titleOfInvention | Process for preparing 3-enol ethers of 11beta-hydroxy-delta4-pregnen-3-ones and derivatives thereof |
| abstract | 1513211 Preparation of 3 - enolethers of 11 - hydroxy - pregnan - 4 - en - 3 - ones SYNTEX (USA) Inc 27 Jan 1976 [18 Feb 1975] 03120/76 Heading C2U A #<SP>3,5</SP>-3-ethyl enol ether of a steroid of the formula wherein R is H, OH, OR<SP>3</SP> or OCOR<SP>3</SP> in which R<SP>3</SP> is C 1-6 alkyl; R<SP>1</SP> is H, OH or OCOR<SP>6</SP> in which R<SP>6</SP> is C alkyl; R<SP>2</SP> is H or α- or #- CH 3 ; or R<SP>1</SP> and R<SP>2</SP> together are in which R<SP>4</SP> and R<SP>6</SP> are each C 1-4 hydrocarbon radicals; and X is H, F, Cl or Br, is prepared by reacting the #<SP>4</SP>-3-one with triethyl orthoacetate in the presence of a strong acid catalyst and in a solvent which consists essentially of 40-100 wt.% of ethanol and 0-60 wt.% of an oxygenated hydrocarbon liquid which is freely miscible with ethanol in all proportions. These liquids include aliphatic ethers and cyclic ethers, and particularly useful are glymes of the formula CH 3 O(CH 2 CH 2 O) n CH 3 wherein n is 1-4. A particularly useful solvent mixture is 50 wt.% ethanol and 50 wt.% glyme. A 6α-halo starting material may be prepared in situ, by placing the corresponding 6#-halosteroid in the solvent containing the acid catalyst and leaving it until epimerizing has been effected before addition of the ortho ester. When the starting material contains free 17α- and 21-hydroxy groups the product will be a 17,21-cyclic-ortho ester and this may subsequently be hydrolysed. The enol etherification may form part of the total process indicated in the following reaction scheme wherein R is alkanoyl and Z is an optional #<SP>1</SP>-double bond may be prepared similarly. Examples illustrate the foregoing procedures and compare the novel enol etherification process with similar known processes. In some examples 11-hydroxy starting materials are converted to 11-unsubstituted-#<SP>9(11)</SP>-steroids during the enol etherification. |
| priorityDate | 1975-02-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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