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(2) For recent reviews of tachykinin receptors and tachykinin receptor antagonists, see (a) Regoli, D.; Boudon, A. Fauchère, J.-L. Pharmacol. Rev. 1994, 46, 551.
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0014286130
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(6) McCarty, F.J.; Rosenstock, P.D.; Paolini, J.P.; Micucci, D.D.; Ashton, L.; Bennetts, W.W.; Palopoli, F.P. J. Med. Chem, 1968, 11, 534.
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Palopoli, F.P.7
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13
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0011348385
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note
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3CN gave good yields, but a lower trans/cis ratio; other acids gave unsatisfactory results.
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14
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0011348386
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note
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3CN) 7.32 - 7.26 (m, 2H), 7.23 - 7.18 (m, 3H), 6.26 - 6.15 (br, 1H), 3.60 (ttd, J=3.8, 11.6 and 7.7 Hz, 1H), 2.96 ( ddd, J= 2.5, 4.2 and 12.0 Hz, 1H), 2.76 - 2.68 (m, 1H), 2.66 - 2.58 (m, 2H), 2.52 (dt, J=2.5 and 12.0 Hz, 1H), 1.80 -1.69 (m, 2H), 1.43 -1.28 (br, 1H), 1.17 (dt, J=4.2 and 12.0 Hz, 1H), 0.90 (q, J=11.6 Hz, 1H).
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15
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0011309549
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note
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10. A concomitantly occurring 2-aza-Cope rearrangement 5a→5c ,which then cyclizes to racemic 6, would explain this result: (equation presented) See for instance: (a) Ref. 11;
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18
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0011316307
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note
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®) of its benzyloxycarbonyl derivative 6.
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19
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0026644849
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(11) To our best knowledge this procedure is the first example of a selective acylation of a secondary amine in presence of a primary amine using an acid chloride as acylating agent. Selective Boc-protection of a secondary amine in presence of a primary amine has been reported: Prugh, J.D.; Birchenough, L.A.; Egbertson, M.S. Synth. Commun. 1992, 22, 2357.
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Synth. Commun.
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Prugh, J.D.1
Birchenough, L.A.2
Egbertson, M.S.3
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20
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0001673091
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Schreiber, S.L., Ed.; Pergamon Press; Oxford
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(12) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2, pp. 1047-1082, Schreiber, S.L., Ed.; Pergamon Press; Oxford, 1991.
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Comprehensive Organic Synthesis
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Hiemstra, H.1
Speckamp, W.N.2
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21
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0025754760
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(13) (a) Esch, P.M.; Boska, I.M.; Hiemstra, H.; de Boer, R.F. and Speckamp, W.N. Tetrahedron 1991, 47, 4039.
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Tetrahedron
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Esch, P.M.1
Boska, I.M.2
Hiemstra, H.3
De Boer, R.F.4
Speckamp, W.N.5
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23
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0001577345
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(14) (a) Paulsen, H.; Todt, K.; Ripperger, H. Chem. Ber. 1968, 101, 3365.
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Chem. Ber.
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Paulsen, H.1
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24
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0000517303
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(b) Chow, Y.L.; Colon, C.J.; Tam, J.N.S. Can. J. Chem. 1968, 46, 2821.
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Chow, Y.L.1
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25
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0015520853
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(15) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
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Shioiri, T.1
Ninomiya, K.2
Yamada, S.3
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27
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0011308647
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note
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(17) A side reaction was the simultaneous cleavage of the benzamide.
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28
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0003020201
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3H-Substance P binding sites
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Skrabanek, P.; Powell, D., Eds.; Boole Press Ltd.; Dublin
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3H-Substance P binding sites", in Substance P - Dublin 1983, Proc. Int. Symp. (1983), pp. 198-199, Skrabanek, P.; Powell, D., Eds.; Boole Press Ltd.; Dublin, 1983.
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Substance P - Dublin 1983, Proc. Int. Symp. (1983)
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Bittiger, H.1
Heid, J.2
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30
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0001295217
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(20) Earle, M.J.; Fairhurst, R,A.; Heaney, H.; Papageorgiou, G. Synlett. 1990, 10, 621.
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Synlett.
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Earle, M.J.1
Fairhurst, R.A.2
Heaney, H.3
Papageorgiou, G.4
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31
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0011353794
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unpublished results
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(21) Veenstra, S.J. unpublished results.
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Veenstra, S.J.1
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