Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

doi:10.3390/cryst2031201

This article is

freely available
re-usable

Crystals 2012, 2(3), 1201-1209; doi:10.3390/cryst2031201

Communication

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

Reik Löser^1,†,* , Martin Nieger² and Michael Gütschow¹

¹ Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, Bonn 53121, Germany ² Laboratory of Inorganic Chemistry, Department of Chemistry, P.O. Box 55, University of Helsinki, Helsinki FIN-00014, Finland ^† Present address: Institut für Radiopharmazie, Helmholtz-Zentrum Dresden-Rossendorf, Bautzner Landstrasse 400, Dresden 01328, Germany.

* Author to whom correspondence should be addressed.

Received: 6 June 2012; in revised form: 20 July 2012 / Accepted: 26 July 2012 / Published: 20 August 2012

Download PDF Full-Text [945 KB, uploaded 20 August 2012 12:29 CEST]

Abstract: The conversion of Z-phenylalanine hydrazide with cyanogen bromide resulted in the formation of the corresponding 2-amino-1,3,4-oxadiazole by spontaneous cyclization of the intermediary cyanohydrazide. The molecular structure of the product was confirmed by single crystal X-ray diffraction. Crystals of the title compound where obtained from a saturated solution in a mixture of petroleum ether and ethyl acetate and belong to the monoclinic space group P2₁ with unit cell parameters a = 9.8152(2) Å, b = 9.6305(2) Å, c = 9.8465(2) Å, β = 116.785(1)°. The asymmetric unit contains one molecule.

Keywords: 1,3,4-oxadiazoles; cyanohydrazides; hydrogen bonds; edge-to-face interactions

Supplementary Files

Supplementary File 1:
CIF-Document (CIF, 18 KB)

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Löser, R.; Nieger, M.; Gütschow, M. Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate. Crystals 2012, 2, 1201-1209.

AMA Style

Löser R, Nieger M, Gütschow M. Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate. Crystals. 2012; 2(3):1201-1209.

Chicago/Turabian Style

Löser, Reik; Nieger, Martin; Gütschow, Michael. 2012. "Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate." Crystals 2, no. 3: 1201-1209.

Crystals EISSN 2073-4352 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert