http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1007756-A

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http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00
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filingDate 1962-07-11-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1965-10-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1007756-A
titleOfInvention New 19-hydroxy-steroids
abstract The invention comprises D 4,6-3-oxo-19-hydroxy-steroids and their 19-esters, and their preparation in which a D 4-3-oxo-6BETA,19-oxido-steroid is treated in an anhydrous medium and in the presence of a strongly acidic catalyst with either an acylating agent to form the 19-ester or with a reactive functional derivative of a lower aliphatic, araliphatic or heterocyclic alcohol to form a 3-enol ether, any enol ether formed is split by treatment with an aqueous acid, if desired, any complex with the catalyst formed is split with an alkaline agent and/or any 2-acyl compound obtained is converted into the corresponding 2-unsubstituted compound by means of an acidic or alkaline agent and/or any D 4,6-3-oxo-19-acyloxy-steroid obtained is hydrolysed or hydrogenolysed to the corresponding 19-ol. The steroids may be of the androstane, pregnane, cholane, cholestane, spirostane or cardanolide series and may contain free, ketalized or enolized oxo groups, free, esterified or etherified hydroxyl groups, alkyl, alkenyl or alkyryl groups and halogen atoms in one or more of positions 1, 2, 7, 8, 9, 11, 12, 14, 15, 16, 17, 20 and 21. They may also contain additional double bonds. The strongly acidic catalyst may be a concentrated mineral or sulphonic acid or a Lewis acid, particularly boron trifluoride, and complexes of this last named compound with D 4,6-2-acetyl-3-oxo-19-acetoxy-pregnadi nes and androstadienes are described and claimed. Suitable acylating agents are anhydrides and halides of lower aliphatic carboxylic acids, and formic acid or mixed anhydrides thereof, and suitable enol-ether-forming reagents are alkyl esters of aliphatic ortho-carboxylic acids. Examples are given, an intermediate in the reaction of D 4-3-oxo - 6BETA,19 - oxido - 17b - acetoxy - androstene with methyl orthoformate being 3,3,5-trimethoxy - 6b ,19 - oxido - 17b - acetoxy - androstane. D 4 - 3,20 - dioxo - 17a - caproyloxy 6b ,19-oxido-pregnene is prepared by preparing D 5-3b -acetoxy - 17a - caproyloxy - 20 - oxo - pregnane from the 17a -ol, converting this to 3b -acetoxy-5a -chloro - 6b - hydroxy - 17a - caproyloxy 20 - oxo - pregnene, converting this to 3b -acetoxy-5a -chloro - 17a - caproyloxy - 20 - oxo - 6b ,19 - oxido-pregnane, hydrolysing this to the 3b -ol, and oxidizing and dehydrochlorinating this. Specifications 994,746, 994,748 and 1,007,757 are referred to.
priorityDate 1961-07-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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