Synthesis of the β3-adrenergic receptor agonist Solabegron and Analogous N-(2-Ethylamino)-β-amino alcohols from O-acylated cyanohydrins - expanding the scope of minor enantiomer recycling

Journal of Organic Chemistry

Volumn 80, Issue 5, 2015, Pages 2937-2941

  Hertzberg, Robin ^a   Monreal Santiago, Guillermo ^a   Moberg, Christina ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

ADRENERGIC RECEPTORS; ENANTIOSELECTIVE TOTAL SYNTHESIS; LEWIS ACID; NOVEL METHODOLOGY; NUCLEOPHILIC SUBSTITUTIONS;

AMINO ALCOHOLS;

(3 CHLOROPHENYL)(CYANO)METHYL 2 BROMOACETATE; 2 BROMOACETYL CYANIDE; 2 [(3,5 DIMETHYLPHENYL)AMINO] N (2 HYDROXY 2 PHENYLETHYL)ACETAMIDE; 3' [[2 [[2 (3 CHLOROPHENYL) 2 HYDROXYETHYL]AMINO]ETHYL]AMINO] [1,1' BIPHENYL] 3 CARBOXYLIC ACID; ALCOHOL DERIVATIVE; CYANO(PHENYL)METHYL (3,5 DIMETHYLPHENYL)GLYCINATE; CYANO(PHENYL)METHYL (4 IODOPHENYL)GLYCINATE; CYANO(PHENYL)METHYL PHENYLGLYCINATE; CYANOHYDRIN; LEWIS ACID; METHYL 3' AMINO [1,1' BIPHENYL] 3 CARBOXYLATE; METHYL 3' [[2 [(3 CHLOROPHENYL)(CYANO)METHOXY] 2 OXOETHYL]AMINO] [1,1' BIPHENYL] 3 CARBOXYLATE; METHYL 3' [[2 [[2 (3 CHLOROPHENYL) 2 HYDROXYETHYL] AMINO] 2 OXOETHYL]AMINO] [1,1' BIPHENYL] 3 CARBOXYLATE; METHYL 3' [[2 [[2 (3 CHLOROPHENYL) 2 HYDROXYETHYL]AMINO]ETHYL]AMINO] [1,1' BIPHENYL] 3 CARBOXYLATE; N (2 HYDROXY 2 PHENYLETHYL) 2 (PHENYLAMINO)ACETAMIDE; SOLABEGRON; UNCLASSIFIED DRUG; ADRENERGIC RECEPTOR STIMULATING AGENT; AMINOALCOHOL; ANILINE DERIVATIVE; BENZOIC ACID DERIVATIVE; BIPHENYL DERIVATIVE; NITRILE;

ACYLATION; ARTICLE; BIOCATALYST; CANDIDA ANTARCTICA; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; HYDROLYSIS; NUCLEOPHILICITY; RACEMIZATION; REDUCTION; SUBSTITUTION REACTION; SUZUKI REACTION; BIOCATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACYLATION; ADRENERGIC AGONISTS; AMINO ALCOHOLS; ANILINE COMPOUNDS; BENZOATES; BIOCATALYSIS; BIPHENYL COMPOUNDS; LEWIS ACIDS; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 84924326489     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00322     Document Type: Article

References (22)

1. Oldenburg, O.; Kribben, A.; Baumgart, D.; Philipp, T.; Erbel, R.; Cohen, M. V. Curr. Opin. Pharmacol. 2002, 2, 740
2. Donaldson, K. H.; Shearer, B. G.; Uehling, D. E. PCT Patent WO9965877A1, 1999.
3. Uehling, D. E.; Shearer, B. G.; Donaldson, K. H.; Chao, E. Y.; Deaton, D. N.; Adkison, K. K.; Brown, K. K.; Cariello, N. F.; Faison, W. L.; Lancaster, M. E.; Lin, J.; Hart, R.; Milliken, T. O.; Paulik, M. A.; Sherman, B. W.; Sugg, E. E.; Cowan, C. J. Med. Chem. 2006, 49, 2758
4. Shearer, B. G.; Chao, E. Y.; Uehling, D. E.; Deaton, D. N.; Cowan, C.; Sherman, B. W.; Milliken, T.; Faison, W.; Brown, K.; Adkison, K. K.; Lee, F. Bioorg. Med. Chem. Lett. 2007, 17, 4670
5. Roy, K. K.; Saxena, A. K. J. Chem. Inf. Model. 2011, 51, 1405
6. Ursino, M. G.; Vasina, V.; Raschi, E.; Crema, F.; De Ponti, F. Pharmacol. Res. 2009, 59, 221
7. Igawa, Y.; Michel, M. C. Naunyn-Schmiedeberg's Arch. Pharmacol. 2013, 386, 177
8. Cooke, J. W. B.; Glover, B. N.; Lawrence, R. M.; Sharp, M. J.; Tymoschenko, M. F. PCT Patent WO2002066418A2, 2002.
9. Zhang, C. PCT Patent WO2010118291A2, 2010.
10. Lawrence, R. M.; Millar, A. PCT Patent WO2001042195A1, 2001.
11. Veum, L.; Pereira, S. R. M.; van der Waal, J. C.; Hanefeld, U. Eur. J. Org. Chem. 2006, 1664
12. Lundgren, S.; Wingstrand, E.; Moberg, C. Adv. Synth. Catal. 2007, 349, 364
13. Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C. J. Am. Chem. Soc. 2005, 127, 11592
14. Wingstrand, E.; Laurell, A.; Fransson, L.; Hult, K.; Moberg, C. Chem. - Eur. J. 2009, 15, 12107
15. Fransson, L.; Laurell, A.; Widyan, K.; Wingstrand, E.; Hult, K.; Moberg, C. ChemCatChem 2010, 2, 683
16. Laurell Nash, A.; Widyan, K.; Moberg, C. ChemCatChem 2014, 6, 3314
17. Belokon, Y. N.; Carta, P.; Gutnov, A. V.; Maleev, V.; Moskalenko, M. A.; Yashkina, L. V.; Ikonnikov, N. S.; Voskoboev, N. V.; Khrustalev, V. N.; North, M. Helv. Chim. Acta 2002, 85, 3301
18. Hertzberg, R.; Moberg, C. J. Org. Chem. 2013, 78, 9174
19. Dear, A. E.; Liu, H. B.; Mayes, P. A.; Perlmutter, P. Org. Biomol. Chem. 2006, 4, 3778
20. Imanishi, M.; Itou, S.; Washizuka, K.; Hamashima, H.; Nakajima, Y.; Araki, T.; Tomishima, Y.; Sakurai, M.; Matsui, S.; Imamura, E.; Ueshima, K.; Yamamoto, T.; Yamamoto, N.; Ishikawa, H.; Nakano, K.; Unami, N.; Hamada, K.; Matsumura, Y.; Takamura, F.; Hattori, K. J. Med. Chem. 2008, 51, 4002
21. Herrmann, K.; Simchen, G. Synthesis 1979, 204
22. Cary, J. M.; Moore, J. S. Org. Lett. 2002, 4, 4663