Title:
キラル的に純粋なβ-アミノアルコールの合成方法
Document Type and Number:
Japanese Patent JP4250529
Kind Code:
B2
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 with 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; and i) recrystallizing the alpha-amino acid to the chirally pure alpha-amino acid. A process is also provided for preparing chirally pure S-enantiomers of 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 further provided for preparing chirally pure S enantiomers of N-sulfonyl beta-amino 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.
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| WO/2007/100086 | LIGAND, METHOD FOR PRODUCING THE SAME, AND CATALYST USING THE LIGAND |
Inventors:
Anthony Frank Cleft
Madeline Miyoko Antein
Derek Cecil Cole
Dennis Martin Kubrak
Lynn Resnick
Joseph Raymond Stock
Jen Wan
Madeline Miyoko Antein
Derek Cecil Cole
Dennis Martin Kubrak
Lynn Resnick
Joseph Raymond Stock
Jen Wan
Application Number:
JP2003551091A
Publication Date:
April 08, 2009
Filing Date:
November 26, 2002
Export Citation:
Assignee:
Wyeth
International Classes:
C07C227/04; A61K31/381; C07B53/00; C07B61/00; C07C209/00; C07C213/00; C07C215/08; C07C229/08; C07C247/12; C07D227/12; C07D263/26; C07D333/32; C07D333/34
Domestic Patent References:
| JP7506100A |
Attorney, Agent or Firm:
Mitsuo Tanaka
Michiko Matsutani
Tadayuki Motoyama
Kenji Tomita
Michiko Matsutani
Tadayuki Motoyama
Kenji Tomita