Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate

A. Salgado, T. Huybrechts, A. Eeckhaut, J. Van der Eycken, Z. Szakonyi, F. Fülöp, A. Tkachev, N. De Kimpe

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]- cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid.

Original languageEnglish
Pages (from-to)2781-2786
Number of pages6
JournalTetrahedron
Volume57
Issue number14
DOIs
Publication statusPublished - Apr 2 2001

Fingerprint

Carboxylic Acids
Hydrolysis
Esterases
Liver
Swine
1,1-dimethylcyclopropane
cyclopropane
cyclopropanecarboxylic acid

Keywords

  • 1-Aminocyclopropane-1-carboxylic acid
  • 2,2-DimethylACC
  • Curtius rearrangement
  • Enzymatic hydrolysis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate. / Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fülöp, F.; Tkachev, A.; De Kimpe, N.

In: Tetrahedron, Vol. 57, No. 14, 02.04.2001, p. 2781-2786.

Research output: Contribution to journalArticle

Salgado, A. ; Huybrechts, T. ; Eeckhaut, A. ; Van der Eycken, J. ; Szakonyi, Z. ; Fülöp, F. ; Tkachev, A. ; De Kimpe, N. / Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate. In: Tetrahedron. 2001 ; Vol. 57, No. 14. pp. 2781-2786.
@article{5ee61b2fcfc1405587cda7580417e00b,
title = "Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate",
abstract = "Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]- cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid.",
keywords = "1-Aminocyclopropane-1-carboxylic acid, 2,2-DimethylACC, Curtius rearrangement, Enzymatic hydrolysis",
author = "A. Salgado and T. Huybrechts and A. Eeckhaut and {Van der Eycken}, J. and Z. Szakonyi and F. F{\"u}l{\"o}p and A. Tkachev and {De Kimpe}, N.",
year = "2001",
month = "4",
day = "2",
doi = "10.1016/S0040-4020(01)00112-0",
language = "English",
volume = "57",
pages = "2781--2786",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "14",

}

TY - JOUR

T1 - Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate

AU - Salgado, A.

AU - Huybrechts, T.

AU - Eeckhaut, A.

AU - Van der Eycken, J.

AU - Szakonyi, Z.

AU - Fülöp, F.

AU - Tkachev, A.

AU - De Kimpe, N.

PY - 2001/4/2

Y1 - 2001/4/2

N2 - Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]- cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid.

AB - Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]- cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid.

KW - 1-Aminocyclopropane-1-carboxylic acid

KW - 2,2-DimethylACC

KW - Curtius rearrangement

KW - Enzymatic hydrolysis

UR - http://www.scopus.com/inward/record.url?scp=0035795078&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035795078&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)00112-0

DO - 10.1016/S0040-4020(01)00112-0

M3 - Article

AN - SCOPUS:0035795078

VL - 57

SP - 2781

EP - 2786

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 14

ER -