Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: Choice of cyanation solvent

Christopher G. Bazewicz; Jacob S. Lipkin; Kristen A. Lozinak; Matthew D. Watson; Scott H. Brewer

doi:10.1016/j.tetlet.2011.10.050

Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: Choice of cyanation solvent

Christopher G. Bazewicz, Jacob S. Lipkin, Kristen A. Lozinak, Matthew D. Watson, Scott H. Brewer

Department of Dermatology

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester and three isotopomers (C¹⁵N, ¹³CN, and ¹³C¹⁵N) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only ∼80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment.

Original language	English (US)
Pages (from-to)	6865-6868
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.050
State	Published - Dec 21 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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@article{37abeb1ee8cd4f56bf03454082847a1e,

title = "Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: Choice of cyanation solvent",

abstract = "N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester and three isotopomers (C15N, 13CN, and 13C15N) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only ∼80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment.",

author = "Bazewicz, {Christopher G.} and Lipkin, {Jacob S.} and Lozinak, {Kristen A.} and Watson, {Matthew D.} and Brewer, {Scott H.}",

note = "Funding Information: We gratefully acknowledge Kristopher Kolonko for helpful discussions; Lisa Mertzman for obtaining materials and supplies; Beth Buckwalter for acquiring NMR spectra; and Carol Strausser for assistance in editing of the manuscript. This work was supported by F&M Hackman funds and NSF (CHE-1053946) to SHB. ",

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doi = "10.1016/j.tetlet.2011.10.050",

language = "English (US)",

volume = "52",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester

T2 - Choice of cyanation solvent

AU - Bazewicz, Christopher G.

AU - Lipkin, Jacob S.

AU - Lozinak, Kristen A.

AU - Watson, Matthew D.

AU - Brewer, Scott H.

N1 - Funding Information: We gratefully acknowledge Kristopher Kolonko for helpful discussions; Lisa Mertzman for obtaining materials and supplies; Beth Buckwalter for acquiring NMR spectra; and Carol Strausser for assistance in editing of the manuscript. This work was supported by F&M Hackman funds and NSF (CHE-1053946) to SHB.

PY - 2011/12/21

Y1 - 2011/12/21

N2 - N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester and three isotopomers (C15N, 13CN, and 13C15N) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only ∼80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment.

AB - N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester and three isotopomers (C15N, 13CN, and 13C15N) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only ∼80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment.

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U2 - 10.1016/j.tetlet.2011.10.050

DO - 10.1016/j.tetlet.2011.10.050

M3 - Article

AN - SCOPUS:81255195897

SN - 0040-4039

VL - 52

SP - 6865

EP - 6868

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: Choice of cyanation solvent

Abstract

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