RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2015; 47(19): 2985-2990
DOI: 10.1055/s-0034-1378848
DOI: 10.1055/s-0034-1378848
paper
2,4-Dimethoxybenzyl Group for the Protection of Tetrazole: An Efficient Synthesis of Olmesartan Medoxomil through C–H Arylation
Weitere Informationen
Publikationsverlauf
Received: 06. Mai 2015
Accepted after revision: 19. Mai 2015
Publikationsdatum:
10. Juli 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201519/lookinside/thumbnails/ss-2015-f0291-op_10-1055_s-0034-1378848-1.jpg)
Abstract
The 2,4-dimethoxybenzyl (DMB) group was found to be effective for protecting tetrazoles. The DMB group is inert to various conditions, including those for ruthenium-catalyzed C–H arylation, but is readily cleaved under mild conditions. The use of a DMB protecting group permitted a synthesis of highly functionalized olmesartan medoxomil in a few steps.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378848.
- Supporting Information
-
References
- 1a The Art of Process Chemistry . Yasuda N. Wiley-VCH; Weinheim: 2011
- 1b Anderson NG. Practical Process Research & Development . Academic Press; San Diego: 2000
- 1c Green Chemistry in the Pharmaceutical Industry . Dunn P, Wells A, Williams MT. Wiley-VCH; Weinheim: 2010
- 2a Seki M. WO 2011061996, 2010
- 2b Seki M. ACS Catal. 2011; 1: 607
- 2c Seki M, Nagahama M. J. Org. Chem. 2011; 76: 10198
- 2d Seki M. Synthesis 2012; 44: 3231
- 2e Seki M. Yuki Gosei Kagaku Kyokaishi 2012; 70: 1295
- 2f Kocienski P. Synfacts 2013; 9: 0006
- 2g Seki M In Science of Synthesis: Catalytic Transformations via C–H Activation. Vol. 1. Yu J.-Q. Thieme; Stuttgart: 2015. in press
- 2h Seki M. WO 2014034868, 2014
- 2i Seki M. WO 2014051008, 2014
- 2j Seki M. RSC Adv. 2014; 4: 29131
- 2k Seki M. Synthesis 2014; 46: 3249
- 2l Seki M. ACS Catal. 2014; 4: 4047
- 2m Seki M. Synthesis 2015; 47: 1423
- 3a Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
- 3b Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 3c Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
-
3d Willis MC. Chem. Rev. 2010; 110: 725
- 3e Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
-
3f Ackermann L. Chem. Commun. 2010; 46: 4866
- 3g Dudnik AS, Gevorgyan V. Angew. Chem. Int. Ed. 2010; 49: 2096
-
3h Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 3i Sun S.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
- 3j Peng HM, Dai L.-X, You S.-L. Angew. Chem. Int. Ed. 2010; 49: 5826
- 3k Ackermann L. Chem. Rev. 2011; 111: 1315
- 3l Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
- 4a Carini DJ, Duncia JV, Aldrich PE, Chiu AT, Johnson AL, Pierce ME, Price WA, Santella III JB, Wells GJ. J. Med. Chem. 1991; 34: 2525
- 4b Bernhart CA, Perreaut PM, Ferrari BP, Muneaux YA, Assens JL. A, Clement J, Haudricourt F, Muneaux CF, Taillades JE. J. Med. Chem. 1993; 36: 3371
- 4c Kubo K, Kohara Y, Yoshimura Y, Inada Y, Shibouta Y, Furukawa Y, Kato T, Nishikawa K, Naka T. J. Med. Chem. 1993; 36: 2343
- 4d Wexler RR, Greenlee WJ, Irvin JD, Goldberg MR, Prendergast K, Smith RD, Timmermans PB. M. W. M. J. Med. Chem. 1996; 39: 625
- 4e Kurup A, Garg R, Carini DJ, Hansch C. Chem. Rev. 2001; 101: 2727
-
5 Trost BM. Science 1991; 254: 1471
- 6 A PMB group was used for the protection of losartan: see refs. 2a and 2c.
- 7a Arockiam PB, Poirier V, Fischmeister C, Bruneau C, Dixneuf PH. Green Chem. 2009; 11: 1871
- 7b Arockiam PB, Fischmeister C, Bruneau C, Dixneuf PH. Angew. Chem. Int. Ed. 2010; 49: 6629
For selected reviews on C–H activation (arylation), see:
For examples, see:
The use of PvOK for C–H arylation of unsubstituted benzyl-protected 1-benzyl-5-phenyl-1H-tetrazole resulted in a higher extent of diarylation (~14%); see ref. 2m. For original papers that describe the use of PvOK for C–H arylation, see: