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inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_9ef6bbdce30e55413c93e18bc12323bc
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publicationDate 2003-06-19-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber CA-2469021-A1
titleOfInvention Process for the synthesis of chirally pure .beta.-amino-alcohols
abstract A process is provided for preparing chirally pure S-enantiomers of .alpha.- amino acids comprising the steps of: a) preparing an organometallic reagent from an alkyl halide of the Formula (R)2CH(CH2)nCH2X; b) adding the organometallic reagent to carbon dioxide to afford a carboxylic acid; c) activating the carboxylic acid with an acid chloride, phosphorus trichloride , acid anhydride, or thionyl chloride in the presence of a tertiary amine base ; d) reacting the product of step c) with an alkali metal salt of S-4-benzyl-2 - oxazolidinone; e) treating the product of step d) with a strong non- nucleophilic base to form an enolate anion; f) trapping the enolate anion wi th 2,4,6-triisopropylbenzenesulfonyl azide to afford an oxazolidinone azide; g) hydrolyzing the oxazolidinone azide with an aqueous base to afford an .alpha .- azido acid; h) reducing the .alpha.-azido acid to the .alpha.-amino acid; an d i) recrystallizing the .alpha.-amino acid to the chirally pure .alpha.-amino acid. A process is also provided for preparing chirally pure S-enantiomers o f .beta.-amino alcohols further comprising the steps of reducing the crude .alpha.-amino acid to the .beta.-amino alcohol and recrystallizing the .beta .- amino alcohol to the chirally pure .beta.-amino alcohol. A process is furthe r provided for preparing chirally pure S enantiomers of N-sulfonyl .beta.-amin o alcohols further comprising the steps of sulfonylating the .beta.-amino alcohol with 5-chloro-thiophene-2-sulfonyl halide; and recrystallizing to afford the chirally pure N-sulfonyl .beta.-amino alcohols.
priorityDate 2001-12-11-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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