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23. General procedurefor 1,2,4-triazole preparation: Thioamide(1 equiv)andhydrazide
(1.2 equiv) were diluted in the minimum of dichloromethane. Silver benzoate
(2 equiv) was then added immediately followed by acetic acid (3 equiv). The
mixture was stirred overnight at room temperature. Distillation of the solvent
under reduced pressure gave a black oil, which was diluted in a solution of
dichloromethane. A flash chromatography on silica gel, eluted with AcOEt/hexane
5/5 to MeOH 5% in AcOEt, afforded the pure triazole in 40–90% yield.
24. Fehrentz, J. A.; Bibian, M.; Moulin, A.; Martinez, J. WO2009/115503.
25. NMR and mass characterization of compound 16b 1H NMR (DMSO-d6,
300 MHz, 28 °C) d (ppm) 1.25 (s, 9H, CH3 Boc), 2.77–2.97 (m, 4H, CH2–CH2–
phenyl), 3.27–3.44 (m, 2H, CH2 b tryptophan), 3.70 (s, 3H, OCH3), 5.05 (q, 1H,
8 Hz, CH
a tryptophan), 5.18 (s, 2H, CH2 p-methoxybenzyl), 6.76 (d, 2H, 9 Hz,
H3 and H5 p-methoxybenzyl), 6.84 (d, 2H, 9 Hz, H2 and H6 p-methoxybenzyl),
6.92 (t, 1H, 8 Hz, H5 tryptophan), 7.03–7.28 (m, 7H, H2 and H6 tryptophan, H2
and H3 H4 H5 and H6 phenethyl), 7.34 (d, 2H, 8 Hz, H4 and H7 tryptophan), 7.73
(d, 1H, 8 Hz, NH Boc), 10.85 (s, 1H, NH tryptophan). 13C{1H} NMR (DMSO-d6,
28 °C):
tryptophan), 31.7 (CH2–CH2–phenyl), 45.8 (CH2–p-methoxyphenyl), 46.4 (CH
tryptophan), 55.1 (OCH3), 78.6 (C quat Boc), 109.3 (C3 tryptophan), 111.3 (C7
d (ppm) 25.9 (CH2–CH2–phenyl), 28.0 (CH3 Boc), 28.3 (CH2 b
a
tryptophan), 114.1 (C3 and C5 p-methoxybenzyl), 118.0 (C4 tryptophan), 118.4
(C5 tryptophan), 120.9 (C6 tryptophan), 124.0 (C2 tryptophan), 126.3 (C4
phenethyl), 126.4 (C1 p-methoxybenzyl), 127.0 (C9 tryptophan), 127.7 (C2 and
C6 p-methoxybenzyl), 128.2 (C2 C3 C5 and C6 phenethyl), 136.0 (C8 tryptophan),
15. Demange, L.; Boeglin, D.; Moulin, A.; Mousseaux, D.; Ryan, J.; Berge, G.; Gagne,
D.; Heitz, A.; Perrissoud, D.; Locatelli, V.; Torsello, A.; Galleyrand, J. C.; Fehrentz,
J. A.; Martinez, J. J. Med. Chem. 2007, 50, 1939–1957.
139.8 (C1 phenethyl), 154.4 (CO Boc), 155.1 and 155.5 (C quat triazole), 158.8
(C4 p-methoxybenzyl). MS (ES), m/z: 552.2 [M+H].