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One-pot efficient synthesis of N(α)-urethane-protected β- and γ-amino acids.

Cal M, Jaremko M, Jaremko Ł, Stefanowicz P - Amino Acids (2012)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Faculty of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, Wroclaw, Poland.

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.

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Scheme of the reaction between N-hydroxyphthalimide and benzyl alcohol
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Fig3: Scheme of the reaction between N-hydroxyphthalimide and benzyl alcohol

Mentions: The reaction described in this paper can also be used for synthesis of anthranilic acid N-urethane-protected derivatives (Fig. 3). However, the yield of this reaction does not exceed 31 %.Fig. 3


One-pot efficient synthesis of N(α)-urethane-protected β- and γ-amino acids.

Cal M, Jaremko M, Jaremko Ł, Stefanowicz P - Amino Acids (2012)

Scheme of the reaction between N-hydroxyphthalimide and benzyl alcohol
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3569585&req=5

Fig3: Scheme of the reaction between N-hydroxyphthalimide and benzyl alcohol
Mentions: The reaction described in this paper can also be used for synthesis of anthranilic acid N-urethane-protected derivatives (Fig. 3). However, the yield of this reaction does not exceed 31 %.Fig. 3

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Faculty of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, Wroclaw, Poland.

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.

Show MeSH