One-pot efficient synthesis of N α-urethane-protected β- And γ-amino acids

Marta Cal; Mariusz Jaremko; Łukasz Jaremko; Piotr Stefanowicz

doi:10.1007/s00726-012-1443-3

One-pot efficient synthesis of N ^α-urethane-protected β- And γ-amino acids

Marta Cal, Mariusz Jaremko^*, Łukasz Jaremko, Piotr Stefanowicz

^*Corresponding author for this work

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

3 Scopus citations

Abstract

1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N ^α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially "one-pot" procedure.

Original language	English (US)
Pages (from-to)	1085-1091
Number of pages	7
Journal	Amino Acids
Volume	44
Issue number	3
DOIs	https://doi.org/10.1007/s00726-012-1443-3
State	Published - Mar 2013
Externally published	Yes

Bibliographical note

Funding Information:
This work was partially supported by Faculty of Chemistry of Wroclaw University, Wrocław, Poland.

Keywords

Anthranilic acid
CBz
GABA
Lossen rearrangement
N -Urethane-protection
N-Hydroxyimides
β- and γ-Amino acids
β-Alanine

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Clinical Biochemistry

Access to Document

10.1007/s00726-012-1443-3

Cite this

@article{556c321630a94440bccc8e22d926b983,

title = "One-pot efficient synthesis of N α-urethane-protected β- And γ-amino acids",

abstract = "1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially {"}one-pot{"} procedure.",

keywords = "Anthranilic acid, CBz, GABA, Lossen rearrangement, N -Urethane-protection, N-Hydroxyimides, β- and γ-Amino acids, β-Alanine",

author = "Marta Cal and Mariusz Jaremko and {\L}ukasz Jaremko and Piotr Stefanowicz",

note = "Funding Information: This work was partially supported by Faculty of Chemistry of Wroclaw University, Wroc{\l}aw, Poland.",

year = "2013",

month = mar,

doi = "10.1007/s00726-012-1443-3",

language = "English (US)",

volume = "44",

pages = "1085--1091",

journal = "Amino Acids",

issn = "0939-4451",

publisher = "Springer",

number = "3",

}

TY - JOUR

T1 - One-pot efficient synthesis of N α-urethane-protected β- And γ-amino acids

AU - Cal, Marta

AU - Jaremko, Mariusz

AU - Jaremko, Łukasz

AU - Stefanowicz, Piotr

N1 - Funding Information: This work was partially supported by Faculty of Chemistry of Wroclaw University, Wrocław, Poland.

PY - 2013/3

Y1 - 2013/3

N2 - 1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially "one-pot" procedure.

AB - 1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially "one-pot" procedure.

KW - Anthranilic acid

KW - CBz

KW - GABA

KW - Lossen rearrangement

KW - N -Urethane-protection

KW - N-Hydroxyimides

KW - β- and γ-Amino acids

KW - β-Alanine

UR - http://www.scopus.com/inward/record.url?scp=84878354520&partnerID=8YFLogxK

U2 - 10.1007/s00726-012-1443-3

DO - 10.1007/s00726-012-1443-3

M3 - Article

C2 - 23250684

AN - SCOPUS:84878354520

SN - 0939-4451

VL - 44

SP - 1085

EP - 1091

JO - Amino Acids

JF - Amino Acids

IS - 3

ER -