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reaction with 1-iodo-4-nitrobenzene (224 mg). Purification by
column chromatography eluting with a petroleum ether–ethyl
acetate gradient afforded 14d (88 mg, 66%) as an oil. Found:
MHϩ 367.1862. C18H27N2O6 requires MH, 367.1869; νmax.(film)/
cmϪ1 3435 (w), 2935 (w), 2306 (w), 1742 (m), 1713 (s), 1606 (w),
1520 (s) and 1348 (s); δH 0.97–1.61 (6H, m), 1.11 (9H, s), 2.39
(2H, t, J 8), 3.41 (3H, s), 3.92–4.04 (1H, m), 4.72 (1H, d, J 8),
6.99 (2H, d, J 8.5), 7.81 (2H, d, J 8.5); δC 24.8 (CH2), 28.3
(3 × CH3), 30.4 (CH2), 32.5 (CH2), 35.5 (CH2), 52.3 (CH3), 53.2
(CH), 79.9 (C), 123.6 (CH), 129.1 (CH), 146.3 (C), 150.1 (C),
155.3 (C), 173.2 (C); m/z 367 (MHϩ); [α]1D7 ϩ11.1 (c = 0.9 in
CH2Cl2).
reaction with 1-iodonaphthalene (0.13 mL). Purification by
column chromatography eluting with a petroleum ether–ethyl
acetate gradient afforded 14h (92 mg, 62%) as an oil. Found:
MHϩ 371.2097 C12H29NO4 requires MH, 371.2096; νmax.(film)/
cmϪ1 3437 (w), 3063 (w), 2981 (m), 2939 (m), 2865 (w), 1742
(s), 1713 (s), 1596 (w) and 1502 (s); δH 1.38 (9H, s), 1.41–1.83
(6H, m), 3.0 (2H, t, J 7.5), 3.65 (3H, s), 4.20–4.31 (1H, m), 4.94
(1H, d, J 7), 7.20–7.48 (4H, m), 7.61–7.67 (1H, m), 7.75–7.80
(1H, m), 7.90–7.99 (1H, m); δC 25.43 (CH2), 28.3 (3 × CH3),
30.3 (CH2), 32.7 (CH2), 32.8 (CH2), 52.2 (CH3), 53.4 (CH), 79.9
(C), 123.8 (CH), 125.4 (CH), 125.5 (CH), 125.7 (CH), 125.95
(CH), 126.6 (CH), 128.8 (CH), 131.8 (CH), 133.9 (C), 138.3 (C),
155.4 (C), 173.4 (C); m/z 371 (MHϩ); [α]1D7 ϩ11.4 (c = 1.75 in
CH2Cl2) .
Methyl (2S )-2-[(tert-butoxycarbonyl)amino]-6-(4-methoxy-
phenyl)hexanoate 14e
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
reaction with 4-iodoanisole (211 mg). Purification by column
chromatography eluting with a petroleum ether–ethyl acetate
gradient afforded 14e (75 mg, 52%) as an oil. Found: MHϩ
352.2118. C19H30NO5 requires MH, 352.2124; νmax.(film)/cmϪ1
2934 (w), 1742 (m), 1713 (s), 1512 (s), 1368 (w), 1246 (m) and
1165 (m); δH 1.27–1.86 (6H, m), 1.43 (9H, s), 2.53 (2H, t, J 7.5),
3.41 (3H, s), 3.77 (3H, s), 4.22–4.33 (1H, m), 5.00 (1H, d, J 8),
6.80 (2H, d, J 8.5), 7.06 (2H, d, J 8.5); δC 24.8 (CH2), 28.3
(3 × CH3), 31.2 (CH2), 32.6 (CH2), 34.7 (CH2), 52.2 (CH3), 53.4
(CH), 55.3 (CH3), 79.8 (C), 113.7 (CH), 129.2 (CH), 134.3 (C),
155.3 (C), 157.7 (C), 173.4 (C); m/z 352 (MHϩ), 374 (MNaϩ);
[α]1D7 ϩ12.1 (c = 1.65 in CH2Cl2).
Methyl 4-{(5S )-5-[(tert-butoxycarbonyl)amino]-6-methoxy-6-
oxohexyl}benzoate 14i
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
reaction with methyl 4-iodobenzoate (236 mg). Purification by
column chromatography eluting with a petroleum ether–ethyl
acetate gradient afforded 14i (53 mg, 35 %) as an oil. Found:
MHϩ 380.2068. C20H30NO6 requires MH, 380.2073; νmax.(film)/
cmϪ1 3437 (w), 2953 (w), 1741 (s), 1716 (s), 1610 (w), 1502 (m),
1284 (s) and 1164 (s); δH 1.37 (9H, s), 1.48–1.83 (6H, m), 2.59
(2H, t, J 8), 3.65 (3H, s), 3.83 (3H, s), 4.16–4.30 (1H, m), 4.93
(2H, d, J 7.5), 7.16 (2H, d, J 8), 7.88 (2H, d, J 8); δC 24.8 (CH2),
28.3 (3 × CH3), 30.5 (CH2), 32.6 (CH2), 35.6 (CH2), 51.9 (CH3),
52.2 (CH), 53.2 (CH3), 79.9 (C), 127.8 (C), 128.4 (CH), 129.7
(CH), 147.7 (C), 155.3 (C), 167.1 (C), 173.3 (C); m/z 380
(MHϩ); [α]1D7 ϩ11.8 (c = 0.85 in CH2Cl2).
Methyl (2S )-2-[(tert-butoxycarbonyl)amino]-6-(2-methyl-
phenyl)hexanoate 14f
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
reaction with 1-iodo-2-methylbenzene (0.11 mL). Purification
by column chromatography eluting with a petroleum ether–
ethyl acetate gradient afforded 14f (35 mg, 26 %) as an oil.
Found: MHϩ 335.2099. C19H30NO5 requires MH, 335.2096;
νmax.(film)/cmϪ1 3430 (w), 2980 (m), 2936 (m), 1742 (s), 1713 (s),
1501 (s), 1365 (s) and 1165 (s); δH 1.38 (9H, s), 1.42–1.82
(6H, m), 2.22 (3H, s), 2.52 (2H, t, J 8), 3.66 (3H, s), 4.19–4.30
(1H, m), 4.94 (1H, d, J 8), 6.98–7.10 (4H, m); δC 19.3 (CH3),
25.3 (CH2), 28.3 (3 × CH3), 29.7 (CH2), 32.8 (CH2), 33 (CH2),
52.2 (CH3), 53.4 (CH), 7 9.9 (C), 125.9 (CH),128.8 (CH), 130.2
(CH), 135.8 (C), 140.4 (C), 155.4 (C), 173.4 (C); m/z 335
(MHϩ); [α]1D7 ϩ22.2 (c = 0.45 in CH2Cl2).
Ethyl 4-{(5S )-5-[(tert-butoxycarbonyl)amino]-6-(6-methoxy-6-
oxohexyl}benzoate 14j
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
reaction with ethyl 4-bromobenzoate (0.15 mL). Purification by
column chromatography eluting with a petroleum ether–ethyl
acetate gradient afforded 14j (115 mg, 73%) as an oil. Found:
MHϩ 394.2238. C21H32NO6 requires MH, 394.2230; νmax.(film)/
cmϪ1 3437 (w), 2983 (m), 2938 (m), 2863 (w), 1741 (s), 1712 (s),
1610 (m), 1502 (s), 1368 (s), 1283 (s), 1165 (s) and 1109 (s);
δH 1.37 (3H, t, J 7), 1.42 (9H, s), 1.47–1.88 (6H, m), 2.64
(2H, t, J 7.5), 3.70 (3H, s), 4.22–4.40 (1H, m), 4.34 (2H, q, J 7),
4.99 (1H, d, J 8), 7.20 (2H, d, J 8), 7.93 (2H, d, J 8); δC 14.3
(CH3), 24.8 (CH2), 28.3 (3 × CH3), 30.6 (CH2), 32.6 (CH2), 35.6
(CH2), 52.2 (CH3), 53.3 (CH), 60.8 (CH2), 79.9 (C), 128.1 (C),
128.4 (CH), 129.6 (CH), 147.6 (C), 155.3 (C), 166.6 (C), 173.3
(C); m/z 394 (MHϩ), 416 (MNaϩ) [α]1D7 ϩ7.4 (c = 1.35 in
CH2Cl2).
Methyl (2S )-2-[(tert-butoxycarbonyl)amino]-6-(4-methyl-
phenyl)hexanoate 14g
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
reaction with 1-iodo-4-methylbenzene (196 mg). Purification by
column chromatography eluting with a petroleum ether–ethyl
acetate gradient afforded 14g (101 mg, 75%) as an oil. Found:
MHϩ 335.2088. C19H30NO5 requires MH, 335.2096; νmax.(film)/
cmϪ1 3437 (w), 2981 (m), 2934 (m), 1742 (s), 1713 (s), 1502 (s)
and 1165 (s); δH 1.29–1.87 (6H, m), 1.43 (9H, s), 2.30 (3H, s),
2.55 (2H, t, J 7.5), 3.71 (3H, s), 4.23–4.34 (1H, m), 4.98 (1H,
d, J 8), 7.00–7.10 (4H, m); δC 20.9 (CH3), 24.8 (CH2), 28.3 (3 ×
CH3), 31.1 (CH2), 32.6 (CH2), 35.1 (CH2), 52.2 (CH3), 53.4
(CH), 79.8 (C), 128.2 (CH), 128.9 (CH), 135.1 (C), 139.1 (C),
155.3 (C), 173.4 (C); m/z 335 (MHϩ); [α]1D7 ϩ7.4 (c = 1.4 in
CH2Cl2).
Methyl (2S )-2-[(tert-butoxycarbonyl)amino]-6-(2-pyridinyl)-
hexanoate 14k
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
reaction with 2-bromopyridine (0.08 mL). Purification by
column chromatography eluting with a petroleum ether–ethyl
acetate gradient afforded 14k (73 mg, 57%) as an oil. Found:
MHϩ 322.1905. C17H26N2O4 requires MH, 322.1892; νmax.(film)/
cmϪ1 3436 (w), 2954 (w), 1743 (m), 1713 (s), 1502 (m), 1268 (s)
and 1165 (s); δH 1.42 (9H, s), 1.55–1.91 (6H, m), 2.77 (2H, t,
J 7.5), 3.71(3H, s), 4.22–4.33 (1H, m), 5.07 (1H, d, J 8), 7.05–
7.15 (2H, m), 7.57 (1H, td, J 7.5, 1.5), 8.51 (1H, d, J 4.5); δC 24.9
(CH2), 28.3 (3 × CH3), 29.3 (CH2), 32.4 (CH2), 37.9 (CH2), 52.2
(CH3), 53.3 (CH), 79.8 (C), 121.0 (CH), 122.7 (CH), 136.3
(CH), 149.2 (CH, 155.4 (C), 161.8 (C), 173.4 (C); m/z 323
(MHϩ); [α]1D7 ϩ7.4 (c = 1.35 in CH2Cl2).
Methyl (2S )-2-[(tert-butoxycarbonyl)amino]-6-(1-naphthyl)-
hexanoate 14h
The title compound was prepared according to the general
hydroboration–Suzuki coupling procedure outlined above by
O r g . B i o m o l . C h e m . , 2 0 0 3 , 1, 9 7 3 – 9 7 7
976