Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, a minor impurity of acyclovir, is described.<em> </em>Starting with commercial <em>N</em>-(9-acetyl-6-o...
Main Authors: | , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2012-07-01
|
Series: | Molecules |
Subjects: | |
Online Access: | http://www.mdpi.com/1420-3049/17/8/8735 |
_version_ | 1819151344661954560 |
---|---|
author | Juan José Vaquero Antonio Cosme Andres Molina José Luis Novella Maria Paz Matía Rosa M. Suárez Julio Alvarez-Builla |
author_facet | Juan José Vaquero Antonio Cosme Andres Molina José Luis Novella Maria Paz Matía Rosa M. Suárez Julio Alvarez-Builla |
author_sort | Juan José Vaquero |
collection | DOAJ |
description | The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, a minor impurity of acyclovir, is described.<em> </em>Starting with commercial <em>N</em>-(9-acetyl-6-oxo-1<em>H</em>-purin-2-yl)acetamide, the process uses an acid catalysed phase transfer catalysis (PTC) process to produce the selective alkylation at the 9 position of the guanine ring. |
first_indexed | 2024-12-22T14:31:55Z |
format | Article |
id | doaj.art-289694840f5243f985b01445ca197ab6 |
institution | Directory Open Access Journal |
issn | 1420-3049 |
language | English |
last_indexed | 2024-12-22T14:31:55Z |
publishDate | 2012-07-01 |
publisher | MDPI AG |
record_format | Article |
series | Molecules |
spelling | doaj.art-289694840f5243f985b01445ca197ab62022-12-21T18:22:43ZengMDPI AGMolecules1420-30492012-07-011788735874110.3390/molecules17088735Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of AcyclovirJuan José VaqueroAntonio CosmeAndres MolinaJosé Luis NovellaMaria Paz MatíaRosa M. SuárezJulio Alvarez-BuillaThe synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, a minor impurity of acyclovir, is described.<em> </em>Starting with commercial <em>N</em>-(9-acetyl-6-oxo-1<em>H</em>-purin-2-yl)acetamide, the process uses an acid catalysed phase transfer catalysis (PTC) process to produce the selective alkylation at the 9 position of the guanine ring.http://www.mdpi.com/1420-3049/17/8/8735nucleosidesacyclovirdrug impuritiesphase transfer catalysis |
spellingShingle | Juan José Vaquero Antonio Cosme Andres Molina José Luis Novella Maria Paz Matía Rosa M. Suárez Julio Alvarez-Builla Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir Molecules nucleosides acyclovir drug impurities phase transfer catalysis |
title | Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir |
title_full | Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir |
title_fullStr | Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir |
title_full_unstemmed | Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir |
title_short | Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir |
title_sort | synthesis of 9 9 1 2 ethanediylbis oxymethylene bis 2 amino 1 9 dihydro 6 lt em gt h lt em gt purin 6 one an impurity of acyclovir |
topic | nucleosides acyclovir drug impurities phase transfer catalysis |
url | http://www.mdpi.com/1420-3049/17/8/8735 |
work_keys_str_mv | AT juanjosevaquero synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir AT antoniocosme synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir AT andresmolina synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir AT joseluisnovella synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir AT mariapazmatia synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir AT rosamsuarez synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir AT julioalvarezbuilla synthesisof9912ethanediylbisoxymethylenebis2amino19dihydro6ltemgthltemgtpurin6oneanimpurityofacyclovir |