Preparation of optically active aliphatic carboxylic acids

C - Chemistry – Metallurgy – 07 – C

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C07C 53/132 (2006.01) C07B 57/00 (2006.01) C07C 51/487 (2006.01) C07C 53/122 (2006.01) C07C 67/60 (2006.01)

Patent

CA 2128520

2128520 9315039 PCTABS00024 A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. In this process: i) a solid racemic mixture of an aliphatic carboxylic acid or ester thereof having formula (I), where R1 is hydrogen or C1 to C6 linear or branched alkyl; R2, R3 and R4 are different and are hydrogen or C1 to C6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C6 to C14 aryl; C1 to C6 alkylthio; C2 to C8 cycloalkylthio; C6 to C10 arylthio; C6 to C10 arylcarbonyl; C4 to C8 cycloalkenyl; trifluoromethyl; halo; or C4 to C5 heteroaryl; is heated to a temperature sufficient to produce a first homogeneous melt; ii) an inorganic or organic base is added to said first homogeneous melt thereby producing a second homogeneous melt; iii) said second homogeneous melt is treated with a chiral organic nitrogenous base; iv) a solid salt that is the reaction product of the chiral organic nitrogenous base and one of the diastereomers in said racemic mixture of the aliphatic carboxylic acid or ester thereof is precipitated from the reaction melt mixture formed in step iii); and v) the precipitated salt is separated.

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