Artículo
Abstract:
The chiral monomer N-(1′-amino-2′-(S)-propyl)-5-oxo-2-(S)- tetrahydrofurancarboxy-amide hydrochloride (11), a precursor of a AABB-type stereoregular polyamide, has been synthesized from pentachlorophenyl 5-oxo-2-(S)-tetrahydrofurancarboxylate (2) and 2-(S)-amino-1-propanol (3). Compounds 2 and 3 are derivatives of the natural amino acids L-glutamic acid and L-alanine, respectively. The regioselective attack of the amino group of 3 to the ester function of 2 led to N-(1′-hydroxy-2′-(S)-propyl)-5-oxo- tetrahydrofurancarboxyamide (4) in 80% yield. However, the tosylation of the primary hydroxyl group of 4, and the subsequent substitution by azide to give 6, took place with low yields. Therefore, an alternative route was conducted starting from 3, which was selectively N-protected as the tert-butyloxycarbonyl derivative (N-Boc), O-tosylated and substituted by azide to afford 1-azido-2-(S)-N-(tert-butyloxycarbonyl)aminopropane (9) in 41% yield from 3. The amino group of 9 was deprotected by acid hydrolysis and the resulting amine 10 was regioselectively condensed with 2 to give the azide derivative 6. Hydrogenolysis of 6 afforded the desired monomer 11 in 69% yield from 2 and 10.
Registro:
| Documento: | Artículo |
| Título: | L-glutamic acid and L-alanine derivatives as building blocks for thesynthesis of a chiral monomer precursor of AABB-type polyamide |
| Autor: | Gómez, R.V.; Orgueira, H.A.; Varela, O. |
| Filiación: | Departamento de Quimica Organica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| Palabras clave: | Chiral monomer; L-alanine; L-alaninol; L-glutamic acid; Stereoregular polyamide; 1 azido 2 (n tert butyloxycarbonyl)aminopropane; 2 amino 1 azidopropane; alanine derivative; alkane derivative; amide; aminopropanol; glutamic acid derivative; monomer; n (1' amino 2' propyl) 5 oxo 2 tetrahydrofuran carboxamide; n (1' azido 2' propyl) 5 oxo 2 tetrahydrofurancarboxyamide; n (1' hydroxy 2' propyl) 5 oxo 2 tetrahydrofurancarboxamide; pentachlorophenyl 5 oxo 2 tetrahydrofurancarboxylate; unclassified drug; article; chirality; hydrogenolysis; hydrolysis; polymerization; synthesis |
| Año: | 2003 |
| Volumen: | 2003 |
| Número: | 10 |
| Página de inicio: | 201 |
| Página de fin: | 208 |
| Título revista: | Arkivoc |
| Título revista abreviado: | Arkivoc |
| ISSN: | 14246376 |
| CAS: | amide, 17655-31-1; aminopropanol, 156-87-6, 78-91-1, 78-96-6 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p201_Gomez |
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Citas:
---------- APA ----------
Gómez, R.V., Orgueira, H.A. & Varela, O. (2003) . L-glutamic acid and L-alanine derivatives as building blocks for thesynthesis of a chiral monomer precursor of AABB-type polyamide. Arkivoc, 2003(10), 201-208.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p201_Gomez [ ]
---------- CHICAGO ----------
Gómez, R.V., Orgueira, H.A., Varela, O. "L-glutamic acid and L-alanine derivatives as building blocks for thesynthesis of a chiral monomer precursor of AABB-type polyamide" . Arkivoc 2003, no. 10 (2003) : 201-208.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p201_Gomez [ ]
---------- MLA ----------
Gómez, R.V., Orgueira, H.A., Varela, O. "L-glutamic acid and L-alanine derivatives as building blocks for thesynthesis of a chiral monomer precursor of AABB-type polyamide" . Arkivoc, vol. 2003, no. 10, 2003, pp. 201-208.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p201_Gomez [ ]
---------- VANCOUVER ----------
Gómez, R.V., Orgueira, H.A., Varela, O. L-glutamic acid and L-alanine derivatives as building blocks for thesynthesis of a chiral monomer precursor of AABB-type polyamide. Arkivoc. 2003;2003(10):201-208.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p201_Gomez [ ]
