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

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...

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Main Authors: Reik Löser, Martin Nieger, Michael Gütschow
Format: Article
Language:English
Published: MDPI AG 2012-08-01
Series:Crystals
Subjects:
Online Access:http://www.mdpi.com/2073-4352/2/3/1201
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author Reik Löser
Martin Nieger
Michael Gütschow
author_facet Reik Löser
Martin Nieger
Michael Gütschow
author_sort Reik Löser
collection DOAJ
description 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.
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spelling doaj.art-4114e85fbda34e50aa1763d078e7cefd2022-12-22T04:09:37ZengMDPI AGCrystals2073-43522012-08-01231201120910.3390/cryst2031201Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamateReik LöserMartin NiegerMichael GütschowThe 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.http://www.mdpi.com/2073-4352/2/3/12011,3,4-oxadiazolescyanohydrazideshydrogen bondsedge-to-face interactions
spellingShingle Reik Löser
Martin Nieger
Michael Gütschow
Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate
Crystals
1,3,4-oxadiazoles
cyanohydrazides
hydrogen bonds
edge-to-face interactions
title Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate
title_full Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate
title_fullStr Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate
title_full_unstemmed Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate
title_short Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate
title_sort synthesis and crystal structure of benzyl 1s 1 5 amino 1 3 4 oxadiazol 2 yl 2 phenylethyl carbamate
topic 1,3,4-oxadiazoles
cyanohydrazides
hydrogen bonds
edge-to-face interactions
url http://www.mdpi.com/2073-4352/2/3/1201
work_keys_str_mv AT reikloser synthesisandcrystalstructureofbenzyl1s15amino134oxadiazol2yl2phenylethylcarbamate
AT martinnieger synthesisandcrystalstructureofbenzyl1s15amino134oxadiazol2yl2phenylethylcarbamate
AT michaelgutschow synthesisandcrystalstructureofbenzyl1s15amino134oxadiazol2yl2phenylethylcarbamate