Page 27 of 44
The Journal of Organic Chemistry
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7.55ꢀ7.48 (m, 1H), 7.47ꢀ7.37 (m, 6H), 7.36 (t, J = 7.6 Hz, 2H), 5.63 (d, J = 8.8 Hz, 1H), 4.71ꢀ4.41
(m, 3H), 4.32 (t, J = 6.6 Hz, 1H), 2.68ꢀ2.49 (m, 2H), 2.31ꢀ2.19 (m, 1H), 2.12 (s, 3H), 2.03ꢀ1.90 (m,
1H); 13C NMR (100 MHz, CDCl3) δ 203. 3, 155.9, 143.7, 143.5, 141.3 (2C), 135.9 (2C), 129.3 (2C),
129.0 (2C), 127.7 (2C), 127.1, 125.6, 124.9 (2C), 120.0 (2C), 67.1, 62.9, 47.2, 31.0, 29.9, 15.3;
FTIR 3286, 2915, 1708, 1690, 1532, 1255, 1053, 740 cmꢀ1. Anal. Calcd for C26H25NO3SSe: C,
61.17; H, 4.94; N, 2.74. Found: C, 60.98; H, 5.19; N, 2.66.
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Se-Phenyl
(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-
yl)propaneselenoate (8h): According to general procedure the title compound was obtained (0.96 g,
85% yield) after chromatography using dichloromethane as eluent: white solid; mp = 180–183 ºC;
[α]24 D ꢀ97.92 (c 0.39, CHCl3); 1H NMR (200 MHz, CDCl3) δ 8.15 (s, 1H), 7.78 (d, J = 7.3 Hz, 2H),
7.58 (t, J = 7.4 Hz, 2H), 7.49ꢀ7.12 (m, 13H), 7.01 (s, 1H), 5.41 (d, J = 8.9 Hz, 1H), 4.93ꢀ4.75 (m,
1H), 4.55 (dd, J = 10.6, 6.8 Hz, 1H), 4.41 (dd, J = 10.6, 6.8 Hz, 1H), 4.23 (t, J = 6.8 Hz, 1H), 3.42
(dd, J = 14.6, 5.1 Hz, 1H), 3.30 (dd, J = 14.6, 5.1 Hz, 1H); 13C NMR δ (50 MHz, CDCl3) 204.4,
155.9, 143.7, 143.5, 141.2 (2C), 136.1, 136.0 (2C), 129.3 (2C), 129.0 (2C), 127.7 (2C), 127.4,
127.1 (2C), 125.9, 125.1 (2C), 123.3, 122.5, 120.0 (2C), 118.6, 11.4, 109.1, 67.3, 63.6, 47.1, 27.5;
FTIR 3473, 3425, 3332, 3054, 1722, 1695, 1532, 1249, 1047, 737 cmꢀ1. Anal. Calcd for
C32H26N2O3Se: C, 67.96; H, 4.63; N, 4.95. Found: C, 67.77; H, 4.95; N, 4.84.
Se-Phenyl (2S)-5-amino-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-oxopentaneselenoate
(8i): According to general procedure the organic solvent was removed to dryness and the residue
was triturated with diethyl ether (2x30 ml). The solid was filtered to afford 8i (0.96 g, 95% yield):
mp = 193–195 ºC; [α]20 ꢀ33.51 (c 0.77, DMF); 1H NMR (200 MHz, DMSOd6) δ 8.42 (d, J = 7.8
D
Hz, 1H), 7.89 (d, J = 7.4, 2H), 7.77 (d, J = 6.8 Hz, 2H), 7.50ꢀ7.21 (m, 10H), 6.82 (br s, 1H), 4.57ꢀ
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4.51 (m, 1H), 4.49ꢀ4.08 (m, 3H), 2.18 (t, J = 7.1 Hz, 2H), 2.10ꢀ1.70 (m, 2H); C NMR (50 MHz,
DMSOd6) δ 204.5, 172.2, 156.3, 143.7 (2C), 140.8 (2C), 135.8 (2C), 129.4 (2C), 128.8, 127.7 (2C),
127.2 (2C), 125.9, 125.3 (2C), 120.2, (2C), 66.0, 63.5, 46.7, 30.7, 26.2; FTIR 3446, 3300, 1720,
1699, 1654, 1544, 1201, 739 cmꢀ1. Anal. Calcd for C26H24N2O4Se: C, 61.54; H, 4.77; N, 5.52.
Found: C, 61.27; H, 5.13; N, 5.45.
Se-Phenyl (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(tritylthio)propaneselenoate
(8j): According to general procedure the organic solvent was removed to dryness and the residue
was triturated with hexane (2x30 ml). The solid was filtered to afford 8j (1.20 g, 83% yield): pale
yellow solid; mp = 176–178 ºC; [α]24 D ꢀ17.74 (c 0.44, CHCl3); 1H NMR (200 MHz, CDCl3) δ7.74ꢀ
7.67 (m, 2H), 7.63ꢀ7.57 (m, 2H), 7.38ꢀ7.12 (m, 24H), 4.91 (d, J = 8.3 Hz, 1H), 4.57 (dd, J = 10.6,
6.5 Hz, 1H), 4.38 (dd, J = 10.6, 6.5 Hz, 1H), 4.21 (t, J = 6.5 Hz, 1H), 4.14 (dt, J = 8.3, 5.5 Hz, 1H),
2.70ꢀ2.55 (m, 2H); 13C NMR δ (50 MHz, CDCl3) 202.7, 155.8, 144.0 (3C), 143.7, 143.6, 141.4 (2C),
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