Isopropyl 2-ethoxyacetate-an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes

Márk Oláh, Zoltán Boros, Gábor Hornyánszky, L. Poppe

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Productivity [conversion (c) and specific reaction rate (r batch or r flow)] and enantiomer selectivity [enantiomeric ratio (E) and enantiomeric excess (ee) of the products] of ethyl and isopropyl esters of acetic, 2-methoxyacetic and 2-ethoxyacetic acids as acylating agents were compared in the N-acylation of (±)-1-phenylethanamine rac-1 catalyzed by variously immobilized forms of Candida antarctica lipase B (CaLB) using shake flasks and continuous-flow reactors. The effect of the temperature in the 0-80 °C range on productivity and enantiomer selectivity in KRs of rac-1 was investigated with the isopropyl esters in continuous-flow mode using CaLB-filled minireactors. Isopropyl 2-ethoxyacetate surpassed the performance of ethyl 2-methoxyacetate in terms of both productivity (1.9-2.9 times higher rate in batch mode) and enantiomeric selectivity (ee (R)-amide>99.9% compared to 99.8%) providing at 40 °C high volumetric productivity (2.22 kg L-1 h-1), specific reaction rate and enantiomeric excess (r flow=783 μmol min-1 g-1, ee (R)-2c >99.9%).

Original languageEnglish
JournalTetrahedron
DOIs
Publication statusAccepted/In press - Oct 19 2015

Fingerprint

Lipase
Amines
Esters
Productivity
Kinetics
Acylation
Enantiomers
Amides
Acetic Acid
Reaction rates
Temperature
Candida antarctica lipase B
methoxyacetic acid
1-phenethylamine
ethoxyacetic acid

Keywords

  • 2-Ethoxyacetic acid esters
  • Acyl donor
  • Continuous-flow biotransformation
  • Kinetic resolution
  • Primary amine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Isopropyl 2-ethoxyacetate-an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes. / Oláh, Márk; Boros, Zoltán; Hornyánszky, Gábor; Poppe, L.

In: Tetrahedron, 19.10.2015.

Research output: Contribution to journalArticle

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AU - Poppe, L.

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