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Efficient Synthesis of New Fluorinated ?-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis.

ABSTRACT: An efficient and novel enzymatic method has been developed for the synthesis of ?-fluorophenyl-substituted ?-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic ?-amino carboxylic ester hydrochloride salts 3a-e in iPr₂O at 45 °C in the presence of Et₃N and H₂O. Adequate analytical methods were developed for the enantio-separation of racemic ?-amino carboxylic ester hydrochlorides 3a-e and ?-amino acids 2a-e. Preparative-scale resolutions furnished unreacted amino esters (R)-4a-e and product amino acids (S)-5a-e with excellent ee values (?99%) and good chemical yields (>48%).

SUBMITTER: Shahmohammadi S

PROVIDER: S-EPMC7766834 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Efficient Synthesis of New Fluorinated β-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis.

Shahmohammadi Sayeh S Fülöp Ferenc F Forró Enikő E

Molecules (Basel, Switzerland) 20201217 24

An efficient and novel enzymatic method has been developed for the synthesis of β-fluorophenyl-substituted β-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic β-amino carboxylic ester hydrochloride salts 3a-e in iPr2O at 45 °C in the presence of Et3N and H2O. Adequate analytical methods were developed for the enantio-separation of racemic β-amino carboxylic ester hydrochlorides 3a- ...[more]

PMID: 33348842

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