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Amino Acid Chlorides: a Journey from Instability and Racemization Toward Broader Utility in Organic Synthesis Including Peptides and Their Mimetics

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Amino Acid Chlorides: a Journey from Instability and Racemization Toward Broader Utility in Organic Synthesis Including Peptides and Their Mimetics Tetrahedron 71 (2015) 2785e2832 Contents lists available at ScienceDirect Tetrahedron journal homepage: www.elsevier.com/locate/tet Tetrahedron report number 1078 Amino acid chlorides: a journey from instability and racemization toward broader utility in organic synthesis including peptides and their mimetics Girish Prabhu a, Basavaprabhu a, N. Narendra b, T. M. Vishwanatha a, Vommina V. Sureshbabu a,* a Room No. 109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B.R. Ambedkar Veedhi, Bangalore University, Bangalore 560 001, India b Department of Chemistry, University College of Science, Tumkur University, B.H. Road, Tumkur 572 103, India article info Article history: Received 13 October 2014 Received in revised form 5 March 2015 Accepted 6 March 2015 Available online 18 March 2015 Dedicated to Professor Padmanabhan Balaram, Indian Institute of Science, Bangalore on the occasion of his superannuation Keywords: Amino acid chlorides Sterically hindered coupling Peptides Peptidomimetics Heterocycles Contents 1. Introduction . ............................................... 2787 2. Chlorinating reagents . ............................................... 2788 3. Preparation and properties . ............................................... 2789 3.1. Urethane protected amino acid chlorides . ......................2789 3.1.1. Cbz- and Boc-chemistry . ......................2789 3.1.2. Fmoc chemistry . ......................2790 3.1.3. Other urethane protecting groups . ......................2790 3.2. Non-urethane protected amino acid chlorides . ......................2791 3.3. Azido acid chlorides . ......................2793 3.4. b- and g-Amino acid chlorides . ......................2793 4. Coupling . ............................................... 2793 4.1. Solution-phase synthesis . ......................2794 4.1.1. SchotteneBaumann conditions . ......................2794 4.1.1.1. Fmoc chemistry . ......................2794 4.1.1.1.1. Continuous solution-phase synthesis . ......................2795 4.1.1.2. Other protecting groups . ......................2795 4.1.2. Non SchotteneBaumann conditions . ......................2798 * Corresponding author. E-mail addresses: [email protected], [email protected], [email protected] (V.V. Sureshbabu). http://dx.doi.org/10.1016/j.tet.2015.03.026 0040-4020/Ó 2015 Elsevier Ltd. All rights reserved. 2786 G. Prabhu et al. / Tetrahedron 71 (2015) 2785e2832 4.1.2.1. Use of co-coupling agents . ......................................2798 4.1.2.2. Metal/metal salts mediated coupling . ..........................2799 4.1.2.2.1. Coupling mediated by commercial zinc dust . ..........................2799 4.1.2.2.2. Microwaves enhanced coupling in the presence of zinc dust . ....................2799 4.1.3. Coupling involving Cbz- and Boc-chemistry . ..........................2800 4.1.4. Coupling involving other protecting groups . ..........................2802 4.1.4.1. Peoc chemistry . .. ......................................2802 4.1.4.2. Tosyl chemistry . ......................................2802 4.1.4.3. Phthaloyl chemistry . ......................................2803 4.2. Solid-phase peptide synthesis . ......................................2803 5. Assembly of sterically hindered peptides . ................... 2804 5.1. Coupling mediated by AgCN . ......................................2804 5.1.1. Cyclic hexapeptides: oxytocin antagonists . ....................................2804 5.2. Coupling of acid chlorides to N-silylated amino esters . ..........................2806 5.3. Assembly of peptides containing N-methyl amino acids . ..........................2806 5.4. Coupling involving Na-benzyl/alkyl-Ca,a-dimethylamino acid ethyl esters . ..........................2807 5.5. Cyclosporins and omphalotin A . ......................................2807 5.6. Petriellin A . .................................................2809 6. Applications . ....................2810 6.1. Amino acid derivatives . ......................................2810 6.1.1. Weinreb amides . ......................................2811 6.1.2. Hydroxamic acids . ......................................2811 6.1.3. 2-CF3-1,3-Oxazolidine (Tfm-pseudoproline) containing dipeptides . ..........................2811 6.1.4. 3,4-Dihydro-4-oxo-1,2,3-benzotriazine-3-yl (Dhbt) and pentafluorophenyl (Pfp) esters . ...............2811 6.1.5. Hydroxyurea and hydantoin derivatives . ......................................2811 6.1.6. Aryl amides . ......................................2811 6.1.7. Diazoketones and homologation to b-amino acids . ..........................2813 6.1.8. FriedeleCrafts reaction: chiral aryl-a-amino ketones . .. ..........................2813 6.1.9. Reaction with Grignard reagent and other organometallic reagents . ..........................2815 6.1.10. Kinetic resolution of heterocyclic amines . ....................................2815 6.2. Heterocycles . .................................................2816 6.2.1. N-Carboxyanhydrides (NCA) and urethane protected N-carboxyanhydrides (UNCAs) . ...................2816 6.2.2. Fused 1,2,5-triazepine-1,5-diones . ......................................2816 6.2.3. Asparagine derived tetrahydropyrimidinones . ..........................2817 6.2.4. a-Methyltryptophan analogs . ......................................2817 6.2.5. Demethoxyfumitremorgin C analogs . ......................................2817 6.2.6. Fumiquinazoline alkaloids . ......................................2817 6.2.7. PicteteSpengler reaction: b-carbolines . .....................................2817 6.2.8. Benzofused bicyclic azepinones . ......................................2818 6.2.9. Substituted hydroxyproline based 2,5-diketopiperazines . ..........................2818 6.2.10. Azetidine-2-ones . ..
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