An Efficient Synthesis of Nα-Protected Amino and Peptide Acid Aryl Amides via Iodine-Mediated Oxidative Acylation of Nα-Protected Amino and Peptide Thioacids

Chilakapati Madhu; T. M. Vishwanatha; Vommina V. Sureshbabu

doi:10.1055/s-0033-1339488

Synthesis, Table of Contents

Synthesis 2013; 45(19): 2727-2736
DOI: 10.1055/s-0033-1339488

paper

An Efficient Synthesis of N^α-Protected Amino and Peptide Acid Aryl Amides via Iodine-Mediated Oxidative Acylation of N^α-Protected Amino and Peptide Thioacids

Authors

Chilakapati Madhu

#109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India Fax: +91(80)22292848 Email: sureshbabuvommina@rediffmail.com Email: hariccb@gmail.com Email: hariccb@hotmail.com
T. M. Vishwanatha

#109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India Fax: +91(80)22292848 Email: sureshbabuvommina@rediffmail.com Email: hariccb@gmail.com Email: hariccb@hotmail.com
Vommina V. Sureshbabu*

#109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India Fax: +91(80)22292848 Email: sureshbabuvommina@rediffmail.com Email: hariccb@gmail.com Email: hariccb@hotmail.com

Abstract

All articles of this category

Abstract

Thioacids derived from N-protected amino or dipeptide and tripeptide acids undergo facile N-acylation with aromatic amines to afford N-protected amino or peptide aryl amides in good to excellent yields and enantiopurities. The method also furnishes difficult-to-prepare N-Fmoc amino acid 4-nitroanilides in good yields. This simple oxidative N^α-acylation of thioacids with aromatic amines proceeds in the presence of iodine, 1-hydroxybenzotriazole and N,N-diisopropylethylamine at room temperature in tetrahydrofuran.

Key words

thioacids - acylation - aryl amides - iodine

Full Text

References

References
1 Pattabiraman VR, Bode JW. Nature 2011; 480: 471
2 Liana AC, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
3 Monatalbetti CA. G. N, Flaque V. Tetrahedron 2005; 61: 10827
4 Liu R, Orgel LE. Nature 1997; 389: 52
5 Dawson PE, Muir TW, Clark-Lewis I, Kent SB. H. Science 1994; 266: 776
6 Hemantha HP, Narendra N, Sureshbabu VV. Tetrahedron 2012; 68: 9491
7 Mende F, Seitz O. Angew. Chem. Int. Ed. 2011; 50: 1232
8 Kato S, Kawahara Y, Kageyama H, Yamada R, Niyomura O, Murai T, Kanda T. J. Am. Chem. Soc. 1996; 118: 1262
9 Wang P, Danishefsky SJ. J. Am. Chem. Soc. 2010; 132: 17045
10 Blake J, Hagman J, Ramachandran J. Int. J. Pept. Prot. Res. 1982; 20: 97
11 Mali SM, Jadhav SV, Gopi HN. Chem. Commun. 2012; 48: 7085

12a Wu E, Zhang Z, Liebeskind LS. J. Am. Chem. Soc. 2011; 133: 14256
12b Pan J, Devarie-Baez NO, Xian M. Org. Lett. 2011; 13: 1092

13a Assem N, Natarajan A, Yudin AK. J. Am. Chem. Soc. 2010; 132: 10986
13b Raz R, Rademann J. Org. Lett. 2012; 14: 5038
13c Mhidia R, Beziere N, Blanpain A, Pommery N, Melnyk O. Org. Lett. 2010; 12: 3982

14a Meegalla SK, Wall MJ, Chen J, Wilson KJ, Ballentine SK, Desjarlais RL, Schubert C, Crysler CS, Chen Y, Molloy CJ, Chaikin MA, Manthey CL, Player MR, Tomczuk BE, Illig CR. Bioorg. Med. Chem. Lett. 2008; 16: 4963
14b Kirkland TA, Adler M, Bauman JG, Jesper MC, Haeggstrom Z, King B, Kochanny MJ, Liang AM, Mendoza L, Phillips GB, Thunnissen M, Trinh L, Whitlow M, Ye B, Ye H, Parkinson J, Guilford WJ. Bioorg. Med. Chem. 2008; 16: 4963
14c Foss FW. Jr, Snyder AH, Davis MD, Rouse M, Okusa MD, Lynch KR, Macdonald TL. Bioorg. Med. Chem. 2007; 15: 663
14d Vinogradov SA. Org. Lett. 2005; 7: 1761
14e Vemparala S, Ivanov I, Pophristic V, Spiegel K, Klein ML. J. Comput. Chem. 2006; 27: 693
14f Yin H, Gerlach LO, Miller MW, Moore DT, Liu D, Vilaire G, Bennett JS, DeGrado WF. Bioorg. Med. Chem. 2006; 16: 3380

15a Kembhavi AA, Buttle DJ, Knight CG, Barrett AJ. Arch. Biochem. Biophys. 1993; 303: 208
15b Stepanov VM, Strongin AY, Izotova LS, Abramov ZT, Lyublinskaya LA, Ermakova LM, Baratova LA, Belyanova LP. Biochem. Biophys. Res. Commun. 1977; 77: 298
15c Ulfohn A, Kramer SP, Calle S, Sass S, Williamson CE, Witten B, Seligman AM. J. Surg. Res. 1968; 8: 345
15d Talanian RV, Quinlan C, Trautz S, Hackett MC, Mankovich JA, Banach D, Ghayur T, Brady KD, Wong WW. J. Biol. Chem. 1997; 272: 9677

16a Fujiwara K, Tsuru D. J. Biol. Chem. 1978; 83: 11
16b Okada Y, Tsuda Y, Hirata A, Nagamatsu Y, Okamoto U. Chem. Pharm. Bull. 1982; 30: 4060
16c Pozdnev V. Int. J. Pept. Prot. Res. 1994; 44: 36
16d Sharma SK, Castellino FJ. Thromb. Res. 1990; 57: 127
16e Kato T, Nagatsu T, Kimura T, Sakakibara S. Experientia 1978; 34: 319
16f Nedev H, Nabarisoa H, Haertle T. Tetrahedron Lett. 1993; 34: 4201
16g Rijkers DT. S, Adams HP. H. M, Hemker HC, Tesser GI. Tetrahedron 1995; 51: 11235
16h Zimmerman M, Yurewicz E, Patel G. Anal. Biochem. 1976; 70: 253
16i Mao L, Wang Z, Li Y, Han X, Zhou W. Synlett 2011; 129

17 Wu X, Hu L. J. Org. Chem. 2007; 72: 765
18 Nuijens T, Cusan C, Kruijtzer JA. W, Rijkers DT. S, Liskamp RM. J, Quaedflieg PJ. L. M. J. Org. Chem. 2009; 74: 5145
19 Kupper FC, Feiters MC, Olofsson B, Kaiho T, Yanagida S, Zimmermann MB, Carpenter LJ, Luther III GW, Lu Z, Jonsson M, Kloo L. Angew. Chem. Int. Ed. 2011; 50: 11598
20 Madhu C, ; Basavaprabhu; Vishwanatha TM, Sureshbabu VV. Tetrahedron Lett. 2012; 53: 1406
21 Basavaprabhu; Vishwanatha TM, Panguluri NR, Sureshbabu VV. Synthesis 2013; 45: 1569
22 Svendsen L, Blomback B, Blomback M, Olsson P. Thromb. Res. 1972; 1: 267

Supplementary Material

Supporting Information (PDF)