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The Journal of Organic Chemistry
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4:1 to 0:1 as the eluent), 0.00381 g, 3%, white solid, mp 199–200 °C; IR (KBr, cm-1) 3409,
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2950, 1744, 1556, 1409; H NMR (300 MHz, CDCl3) δH 7.17 (d, J = 8.7 Hz, 2H), 7.07 (d, J =
8.7 Hz, 2H), 6.36 (br, 1H), 6.00 (br, 1H), 5.37 (br, 1H), 5.00–4.97 (br, 1H), 4.23 (br, 1H), 3.86–
3.64 (m, 1H), 2.83–2.74 (m, 2H), 2.26–2.13 (m, 3H), 2.00– 1.76 (m, 2H), 1.55 (s, 9H), 1.42 (s,
9H), 0.89–0.73 (m, 6H); 13C{1H} NMR (125 MHz, CDCl3) δC 176.7, 175.4, 156.0, 151.8, 149.9,
134.9, 130.0, 121.3, 83.5, 80.0, 60.5, 56.1, 50.2, 40.9, 32.3, 30.9, 30.3, 28.2, 27.6, 19.1, 17.7;
HRMS (FAB) calcd for (M+H)+ C26H42N3O7: 508.3023, found 508.3017.
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rac-(2S,
4R,
4aS)
and
(2R,
4S,
4aR)-2-N-(N’-Boc-Val)-amino-4-carbonyl[ValVal(OMe)]-6-O-Boc-oxy-1,2,3,4,4a,7-hexahydr
onaphthalene (3dJ)): (using chloroform/acetone = 1:0 to 3:1 as the eluent), 0.0523 g, 29%,
white solid, mp 244–245 °C; IR (KBr, cm-1) 3381, 2940, 1753, 1643, 1547; 1H NMR (300 MHz,
CDCl3) δH 6.63 (br, 2H), 5.51 (br, 1H), 5.35 (br, 1H), 5.17 (br, 1H), 4.50–4.46 (m, 1H), 4.30–
4.25 (m, 1H), 4.00 (br, 1H), 3.84 (br, 1H), 3.71 (s, 3H), 3.06–3.02 (m, 1H), 2.83 (br, 2H), 2.63–
2.57 (m, 1H), 2.24–1.87 (m, 7H), 1.47 (s, 9H), 1.43 (s, 9H), 0.86–0.99 (m, 18H); 13C{1H} NMR
(125 MHz, CDCl3) δC 173.2, 172.0, 171.6, 171.0, 156.0, 151.1, 146.8, 133.0, 118.6, 112.4, 82.8,
79.5, 59.2, 59.0, 57.4, 51.8, 50.7, 47.5, 41.4, 40.1, 35.6, 32.0, 30.6, 30.5, 28.4, 27.6, 19.1, 18.9,
18.1, 18.0; HRMS (FAB) calcd for (M+H)+ C37H61N4O10: 721.4387, found 721.4374.
rac-(2S,
4S,
4aS)
and
(2R,
4R,
4aR)-N-2-(N’-Boc-Val)-amino-4-carbonyl[ValVal(OMe)]-6-O-Boc-oxy-1,2,3,4,4a,7-hexahydr
onaphthalene (4dJ): (using chloroform/acetone = 1:0 to 3:1 as the eluent), 0.0108 g, 6%, white
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solid, mp 222–223 °C; IR (KBr, cm-1) 3385, 2950, 1748, 1647, 1528; H NMR (300 MHz,
CDCl3) δH 6.96 (br, 1H), 6.35–6.30 (m, 1H), 5.50–5.44 (m, 2H), 5.18–5.12 (m, 1H), 4.60–4.52
(m, 1H), 4.25–4.18 (m, 1H), 4.01–3.90 (m, 2H), 3.71 (s, 3H), 2.95 (br, 1H), 2.82 (br, 2H), 2.52–
2.47 (m, 1H), 2.25–1.92 (m, 7H), 1.49 (s, 9H), 1.43 (s, 9H), 0.98–0.86 (m, 18H); 13C{1H} NMR
(125 MHz, CDCl3) δC 172.1, 171.1, 170.8, 155.8, 151.5, 146.8, 132.7, 119.0, 112.7, 82.9, 79.8,
59.4, 57.0, 51.9, 50.7, 47.3, 40.7, 36.4, 31.7, 30.6, 30.3, 28.3, 27.6, 19.3, 17.8, 19.1, 19.0, 18.1;
HRMS (FAB) calcd for (M+H)+ C37H61N4O10: 721.4387, found 721.4380.
4-N-(N’-Boc-Val)-amino-5-(4’-O-Boc-phenoxy)-N-[ValVal(OMe)]pentylamide (5dJ): (using
chloroform/acetone = 1:0 to 3:1 as the eluent), 0.0216 g, 12%, white solid, mp 201–202 °C; IR
(KBr, cm-1) 3376, 2936, 1757, 1523, 1423; 1H NMR (300 MHz, CDCl3) δH 7.40–7.37 (br, 1H),
7.20–7.16 (m, 2H), 7.07–7.02 (m, 2H), 6.70–6.55 (m, 2H), 5.13–5.10 (br, 1H), 4.58–4.54 (m,
1H), 4.29–4.16 (m, 2H), 3.83–3.69 (m, 4H), 2.79–2.70 (m, 2H), 2.22–1.83 (m, 7H), 1.54 (s, 9H),
1.43 (s, 9H), 1.00–0.74 (m, 18H); 13C{1H} NMR (125 MHz, CDCl3) δC 173.6, 172.6, 172.3,
171.9, 151.7, 149.6, 135.6, 130.1, 121.1, 83.4, 79.9, 60.4, 59.5, 57.1, 52.2, 50.1, 41.0, 32.2, 31.1,
30.3, 29.5, 28.3, 27.6, 19.3, 19.1, 18.9, 18.5, 18.2, 17.8; HRMS (FAB) calcd for (M+H)+
C37H61N4O10: 721.4387, found 721.4377.
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