Prostaglandin intermediate 2-oxo-alkyl-phosphonic acid ester derivs. - prepd. by reacting omega-substd. carboxylic acid ester(s) with di:alkyl alkyl-phosphonate alkali salts

New 2-oxo-alkylphosphonic acid dialkyl esters are cpds. of formula (I): where R1 = alkyl; R2-R5 = H or opt. substd. alkyl; n = 0-8; X = CN, alkoxy carbonyl or N,N-disubstd. carbamoyl. (I) are useful as intermediates for prostaglandin analoges of formulae (V) and (VI) (where M is O or H, OH) which ha...

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Bibliographic Details
Main Authors OEDIGER,HERMANN,DR, LIEB,FOLKER,DR
Format Patent
LanguageEnglish
German
Published 21.09.1978
Edition2
Subjects
ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:New 2-oxo-alkylphosphonic acid dialkyl esters are cpds. of formula (I): where R1 = alkyl; R2-R5 = H or opt. substd. alkyl; n = 0-8; X = CN, alkoxy carbonyl or N,N-disubstd. carbamoyl. (I) are useful as intermediates for prostaglandin analoges of formulae (V) and (VI) (where M is O or H, OH) which have a narrower profile of activity (i.e. fewer undesired side effects I and longer duration of action than natural prostaglandins. Specific cpds. (I) include 6-tert-butoxycarbonyl-2-oxo-hexylphosphonic acid dimethyl ester. In an example, this is prepd. by heating dimethyl methylphosphonate in THF with butyl-lithium at -70 to -78 degrees C and reacting with methyl tert-butyl adipate at -70 to-78 degrees C.
Bibliography:Application Number: DE19772711009