A Facile Synthesis of Azetidin-2-ylphosphonic Acid and Its 1-Alkyl Derivatives

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Title:A Facile Synthesis of Azetidin-2-ylphosphonic Acid and Its 1-Alkyl Derivatives
Creators:
Otmar, Miroslav
Poláková, Lucie
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 3, pp. 507-516
Uncontrolled Keywords:Phosphonopeptides, Cyclizations, Azetidines, Phosphonates, Hydrolysis, Amino acids analogs, Aminophosphonates

Abstract

Treatment of racemic diisopropyl [1,3-bis(mesyloxy)propyl]phosphonate with allyl-, benzyl-, 2-hydroxyethyl-, or propylamine gave the corresponding diisopropyl [(3-(alkylamino)-1-(mesyloxy)propyl]phosphonates. Heating of their toluene solution with aqueous potassium carbonate effected a cyclization to diisopropyl (1-alkylazetidin-2-yl)phosphonates. In the 1-benzyl- and [1-(2-hydroxyethyl)azetidin-2-yl]phosphonate, the isopropyl ester groups were removed by treatment with bromotrimethylsilane which gave 1-benzyl- and [1-(2-hydroxyethyl)azetidin-2-yl]phosphonic acid. Following hydrogenolysis of the benzyl group afforded azetidin-2-ylphosphonic acid. <p>

Title:A Facile Synthesis of Azetidin-2-ylphosphonic Acid and Its 1-Alkyl Derivatives
Creators:
Otmar, Miroslav
Poláková, Lucie
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Phosphonopeptides, Cyclizations, Azetidines, Phosphonates, Hydrolysis, Amino acids analogs, Aminophosphonates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:3
Page Range:pp. 507-516
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20010507UNSPECIFIED
ID Code:1806
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Otmar, Miroslav; Poláková, Lucie; Masojídková, Milena; Holý, Antonín (2001) A Facile Synthesis of Azetidin-2-ylphosphonic Acid and Its 1-Alkyl Derivatives. Collection of Czechoslovak Chemical Communications, 66 (3). pp. 507-516. ISSN 0010-0765

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