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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 of obtaining Nα-urethane-protected β-alanine and γ-aminopropionic acid (GABA) derivatives
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Fig2: Scheme of the reaction of obtaining Nα-urethane-protected β-alanine and γ-aminopropionic acid (GABA) derivatives

Mentions: The aryl- and alkylsulfonates of hydroxyimides form the product I, which is next hydrolyzed with 1 M methanolic NaOH solution forming N-urethane-protected amino acid. Then the reaction mixture is acidified to pH 1 with 5 M HCl and the product II crystallizes spontaneously or is extracted with ethyl acetate which is subsequently removed in vacuo (Fig. 2). The yield of β-alanine derivatives synthesized by this procedure is in the range of 38–82 %. The lowest yield is obtained when benzene is used as a solvent (38 %), the highest—when 4-methoxybenzyl alcohol is used (82 %). However, all the results are much higher than those obtained for other reported methods of synthesis of β-alanine-containing compounds (Ranganathan et al. 1997).Fig. 2


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 of obtaining Nα-urethane-protected β-alanine and γ-aminopropionic acid (GABA) derivatives
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig2: Scheme of the reaction of obtaining Nα-urethane-protected β-alanine and γ-aminopropionic acid (GABA) derivatives
Mentions: The aryl- and alkylsulfonates of hydroxyimides form the product I, which is next hydrolyzed with 1 M methanolic NaOH solution forming N-urethane-protected amino acid. Then the reaction mixture is acidified to pH 1 with 5 M HCl and the product II crystallizes spontaneously or is extracted with ethyl acetate which is subsequently removed in vacuo (Fig. 2). The yield of β-alanine derivatives synthesized by this procedure is in the range of 38–82 %. The lowest yield is obtained when benzene is used as a solvent (38 %), the highest—when 4-methoxybenzyl alcohol is used (82 %). However, all the results are much higher than those obtained for other reported methods of synthesis of β-alanine-containing compounds (Ranganathan et al. 1997).Fig. 2

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