http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-1461303-A2

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filingDate 2002-11-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_af9af91e15b531b144daf1c7a79fac9c
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publicationDate 2004-09-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-1461303-A2
titleOfInvention PROCESS FOR THE SYNTHESIS OF CHIRALLY PURE b-AMINO-ALCOHOLS
abstract A process is provided for preparing chirally pure S-enantiomers of α-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 with 2,4,6-triisopropylbenzenesulfonyl azide to afford an oxazolidinone azide; g) hydrolyzing the oxazolidinone azide with an aqueous base to afford an α-azido acid; h) reducing the α-azido acid to the α-amino acid; and i) recrystallizing the α-amino acid to the chirally pure α-amino acid. A process is also provided for preparing chirally pure S-enantiomers of β-amino alcohols further comprising the steps of reducing the crude α-amino acid to the β-amino alcohol and recrystallizing the β-amino alcohol to the chirally pure β-amino alcohol. A process is further provided for preparing chirally pure S enantiomers of N-sulfonyl β-amino alcohols further comprising the steps of sulfonylating the β-amino alcohol with 5-chloro-thiophene-2-sulfonyl halide; and recrystallizing to afford the chirally pure N-sulfonyl β-amino alcohols.
priorityDate 2001-12-11-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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