Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative

J. Schindler, Márton Egressy, Laura Bereczki, G. Pokol, E. Fogassy, K. Marthi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dicarboxilic acid derivatized resolving agents of racemic 1-phenylethylamine. Resolution results obtained with the oxalic, malonic, and succinic acid derivatives were previously discussed. Each of the above derivative resolving agents could be successfully applied as resolving agents of 1-phenylethylamine. The efficiency of the present optical resolution using (+)-(R)-N-(1-phenylethyl)glutaramic acid resolving agent was remarkably inferior to the results obtained by its shorter chained homologues. Use of achiral additives, like urea, thiourea, N-methylurea, and N,N′-dimethylurea caused large increase in the efficiency of the resolution by (+)-(R)-N-(1-phenylethyl) glutaramic acid resolving agent Precipitated salts obtained in the resolutions performed in the presence of the additives were investigated by thermoanalysis, X-ray powder diffraction, and optical microscopy. Based on the analytical data, the improvement of the resolution results was attributed to the influence of the additives on the crystal nucleation processes of the diasteromeric salts.

Original languageEnglish
Pages (from-to)239-244
Number of pages6
JournalChirality
Volume19
Issue number3
DOIs
Publication statusPublished - 2007

Fingerprint

Phenethylamines
Derivatives
Acids
Salts
Powder Diffraction
Oxalic Acid
Thiourea
Succinic Acid
Amides
X-Ray Diffraction
Urea
Microscopy
X ray powder diffraction
Thermoanalysis
Optical microscopy
glutaric acid
Thioureas
Nucleation
glutaramic acid
Crystals

Keywords

  • Conglomerate
  • Crystal nucleation
  • Derivative-derivative resolution
  • Improvement of optical purity
  • Optical microscopy
  • Resolution efficiency
  • Urea

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative. / Schindler, J.; Egressy, Márton; Bereczki, Laura; Pokol, G.; Fogassy, E.; Marthi, K.

In: Chirality, Vol. 19, No. 3, 2007, p. 239-244.

Research output: Contribution to journalArticle

@article{d6380ef4fd454389ad400257dbd0176c,
title = "Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative",
abstract = "Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dicarboxilic acid derivatized resolving agents of racemic 1-phenylethylamine. Resolution results obtained with the oxalic, malonic, and succinic acid derivatives were previously discussed. Each of the above derivative resolving agents could be successfully applied as resolving agents of 1-phenylethylamine. The efficiency of the present optical resolution using (+)-(R)-N-(1-phenylethyl)glutaramic acid resolving agent was remarkably inferior to the results obtained by its shorter chained homologues. Use of achiral additives, like urea, thiourea, N-methylurea, and N,N′-dimethylurea caused large increase in the efficiency of the resolution by (+)-(R)-N-(1-phenylethyl) glutaramic acid resolving agent Precipitated salts obtained in the resolutions performed in the presence of the additives were investigated by thermoanalysis, X-ray powder diffraction, and optical microscopy. Based on the analytical data, the improvement of the resolution results was attributed to the influence of the additives on the crystal nucleation processes of the diasteromeric salts.",
keywords = "Conglomerate, Crystal nucleation, Derivative-derivative resolution, Improvement of optical purity, Optical microscopy, Resolution efficiency, Urea",
author = "J. Schindler and M{\'a}rton Egressy and Laura Bereczki and G. Pokol and E. Fogassy and K. Marthi",
year = "2007",
doi = "10.1002/chir.20377",
language = "English",
volume = "19",
pages = "239--244",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "3",

}

TY - JOUR

T1 - Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative

AU - Schindler, J.

AU - Egressy, Márton

AU - Bereczki, Laura

AU - Pokol, G.

AU - Fogassy, E.

AU - Marthi, K.

PY - 2007

Y1 - 2007

N2 - Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dicarboxilic acid derivatized resolving agents of racemic 1-phenylethylamine. Resolution results obtained with the oxalic, malonic, and succinic acid derivatives were previously discussed. Each of the above derivative resolving agents could be successfully applied as resolving agents of 1-phenylethylamine. The efficiency of the present optical resolution using (+)-(R)-N-(1-phenylethyl)glutaramic acid resolving agent was remarkably inferior to the results obtained by its shorter chained homologues. Use of achiral additives, like urea, thiourea, N-methylurea, and N,N′-dimethylurea caused large increase in the efficiency of the resolution by (+)-(R)-N-(1-phenylethyl) glutaramic acid resolving agent Precipitated salts obtained in the resolutions performed in the presence of the additives were investigated by thermoanalysis, X-ray powder diffraction, and optical microscopy. Based on the analytical data, the improvement of the resolution results was attributed to the influence of the additives on the crystal nucleation processes of the diasteromeric salts.

AB - Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dicarboxilic acid derivatized resolving agents of racemic 1-phenylethylamine. Resolution results obtained with the oxalic, malonic, and succinic acid derivatives were previously discussed. Each of the above derivative resolving agents could be successfully applied as resolving agents of 1-phenylethylamine. The efficiency of the present optical resolution using (+)-(R)-N-(1-phenylethyl)glutaramic acid resolving agent was remarkably inferior to the results obtained by its shorter chained homologues. Use of achiral additives, like urea, thiourea, N-methylurea, and N,N′-dimethylurea caused large increase in the efficiency of the resolution by (+)-(R)-N-(1-phenylethyl) glutaramic acid resolving agent Precipitated salts obtained in the resolutions performed in the presence of the additives were investigated by thermoanalysis, X-ray powder diffraction, and optical microscopy. Based on the analytical data, the improvement of the resolution results was attributed to the influence of the additives on the crystal nucleation processes of the diasteromeric salts.

KW - Conglomerate

KW - Crystal nucleation

KW - Derivative-derivative resolution

KW - Improvement of optical purity

KW - Optical microscopy

KW - Resolution efficiency

KW - Urea

UR - http://www.scopus.com/inward/record.url?scp=33847187445&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33847187445&partnerID=8YFLogxK

U2 - 10.1002/chir.20377

DO - 10.1002/chir.20377

M3 - Article

C2 - 17230500

AN - SCOPUS:33847187445

VL - 19

SP - 239

EP - 244

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 3

ER -