Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid

A convenient and practical synthesis of imidazol-1-yl-acetic acid hydrochloride was achieved via N-alkylation of imidazole using tert-butyl chloroacetate followed by a non-aqueous ester cleavage of the resulting imidazol-1-yl-acetic acid tert-butyl ester in the presence of titanium tetrachloride. Th...

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Autores principales: Singh, Santosh Kumar, Manne, Narendra, Ray, Purna Chandra, Pal, Manojit
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2605618/
https://www.ncbi.nlm.nih.gov/pubmed/19104672
http://dx.doi.org/10.3762/bjoc.4.42
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author Singh, Santosh Kumar
Manne, Narendra
Ray, Purna Chandra
Pal, Manojit
author_facet Singh, Santosh Kumar
Manne, Narendra
Ray, Purna Chandra
Pal, Manojit
author_sort Singh, Santosh Kumar
collection PubMed
description A convenient and practical synthesis of imidazol-1-yl-acetic acid hydrochloride was achieved via N-alkylation of imidazole using tert-butyl chloroacetate followed by a non-aqueous ester cleavage of the resulting imidazol-1-yl-acetic acid tert-butyl ester in the presence of titanium tetrachloride. The synthesized imidazol-1-yl-acetic acid hydrochloride was then utilized to prepare zoledronic acid.
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spelling pubmed-26056182008-12-22 Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid Singh, Santosh Kumar Manne, Narendra Ray, Purna Chandra Pal, Manojit Beilstein J Org Chem Full Research Paper A convenient and practical synthesis of imidazol-1-yl-acetic acid hydrochloride was achieved via N-alkylation of imidazole using tert-butyl chloroacetate followed by a non-aqueous ester cleavage of the resulting imidazol-1-yl-acetic acid tert-butyl ester in the presence of titanium tetrachloride. The synthesized imidazol-1-yl-acetic acid hydrochloride was then utilized to prepare zoledronic acid. Beilstein-Institut 2008-11-17 /pmc/articles/PMC2605618/ /pubmed/19104672 http://dx.doi.org/10.3762/bjoc.4.42 Text en Copyright © 2008, Singh et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Singh, Santosh Kumar
Manne, Narendra
Ray, Purna Chandra
Pal, Manojit
Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid
title Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid
title_full Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid
title_fullStr Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid
title_full_unstemmed Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid
title_short Synthesis of imidazol-1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid
title_sort synthesis of imidazol-1-yl-acetic acid hydrochloride: a key intermediate for zoledronic acid
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2605618/
https://www.ncbi.nlm.nih.gov/pubmed/19104672
http://dx.doi.org/10.3762/bjoc.4.42
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AT raypurnachandra synthesisofimidazol1ylaceticacidhydrochlorideakeyintermediateforzoledronicacid
AT palmanojit synthesisofimidazol1ylaceticacidhydrochlorideakeyintermediateforzoledronicacid

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