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HETEROCYCLES, Vol. 73, 2007
amide rotamers): δ 0.88 (t, J = 6.9 Hz, 3H), 1.23-1.38 (m, 18H), 1.58-1.60 (m, 2H), 2.90-3.00 (m, 2H),
4.01 (s, 2H of a rotamer), 4.33 (s, 2H of a rotamer), 4.63 (s, 2H of a rotamer), 4.83 (s, 2H of a rotamer),
13
7.13-7.54 (m, 10H); C NMR (CDCl3, 100 MHz): δ 14.1, 22.7, 28.7, 28.9, 29.1, 29.3, 29.5, 29.6, 31.9,
49.2, 54.0, 57.5, 126.9, 129.0, 128.6, 128.3, 128.0, 127.1, 130.0, 135.2, 135.9, 172.4, 196.4; HRMS
(FAB+): calcd for C28H39NO2S453.2701 (M+), found 453.2722.
S-1-Dodecyl 2-(N-benzylbenzamido)propanethioate (16c).
The reaction of N-acyloxazolidinone 11c (130 mg, 0.342 mmol), n-BuLi (1.0 M solution in hexane, 0.35
mL, 0.35 mmol) and n-dodecanethiol (0.41 mL, 1.71 mmol) in THF (net 4.0 mL) was carried out
following the general procedure (10 min) to provide 16c (120 mg, 75%) as a white solid. IR (film, cm-1):
1
955, 1316, 1402, 1452, 1462, 1651, 1656, 1680, 1691, 1726, 2314, 2854, 2925; H NMR (CDCl3, 400
MHz): δ 0.86-0.90 (m, 3H), 1.26-1.36 (m, 21H), 1.50-1.64 (m, 2H), 2.83-2.96 (m, 2H), 4.62 (d, J = 6.8
Hz, 1H), 4.66 (d, J = 7.0 Hz, 1H), 5.27-5.42 (m, 1H), 7.25-7.50 (m, 10H); 13C NMR (CDCl3, 100 MHz): δ
14.1, 22.7, 28.9, 29.1, 29.4, 29.5, 29.6, 29.7, 31.9, 46.9, 126.6, 126.8, 127.1, 127.5, 128.6, 129.8, 136.0,
137.3, 170.9, 199.5; HRMS (FAB+): calcd for C29H41NO2S467.2858 (M+), found 467.2871.
S-1-Dodecyl 2-(N-benzylbenzamido)-2-phenylethanethioate (16d).
The reaction of N-acyloxazolidinone 11d (48 mg, 0.109 mmol), n-BuLi (1.37 M solution in hexane, 0.16
mL, 0.22 mmol) and n-dodecanethiol (0.14 mL, 0.58 mmol) in THF (net 2.5 mL) was carried out
following the general procedure (10 min) to provide 16d (38 mg, 66%) as a pale-yellow oil. IR (film,
1
cm-1): 723, 1001, 1395, 1454, 1496, 1647, 1685, 2854, 2925; H NMR (CDCl3, 400 MHz): δ 0.88 (t, J =
6.8 Hz, 3H), 1.25-1.31 (m, 18H), 1.53-1.62 (m, 2H), 2.93 (t, J = 5.3 Hz, 2H), 4.33 (s, 1H), 4.37 (s, 1H),
13
5.74 (s, 1H), 6.83-6.92 (m, 2H), 7.11-7.12 (m, 3H), 7.25-7.49 (m, 8H), 7.49-7.52 (m, 2H); C NMR
(CDCl3, 100 MHz): δ 14.1, 22.7, 28.9, 29.1, 29.3, 29.4, 29.5, 29.6, 31.9, 52.2, 69.6, 126.8, 128.2, 128.5,
128.6, 128.9, 129.9, 130.2, 130.5, 130.6, 133.8, 135.9, 137.2, 173.0, 197.3; HRMS (FAB+): calcd for
C34H43NO2S529.3014 (M+), found 529.3004.
S-1-Dodecyl 2-(N-benzylacetamido)-3-methylbutanethioate (16e).
The reaction of N-acyloxazolidinone 11e (59 mg, 0.17 mmol), n-BuLi (1.37 M solution in hexane, 0.25
mL, 0.34 mmol) and n-dodecanethiol (0.21 mL, 0.88 mmol) in THF (net 3.0 mL) was carried out
following the general procedure (10 min) to provide 16e (61 mg, 78%) as a pale yellow oil. IR (film,
1
cm-1): 728, 802, 1144, 1255, 1405, 1457, 1662, 1684, 2854, 2925; H NMR (CDCl3, 400 MHz): δ
0.77-0.97 (m, 9H), 1.25-1.27 (m, 18H), 1.41-1.47 (m, 2H), 2.02 (s, 3H), 2.32-2.33 (m, 1H), 2.69-2.76 (m,
2H), 4.50-4.73 (m, 2H), 5.23 (d, J = 11 Hz, 1H), 7.15-7.30 (m, 5H); 13C NMR (CDCl3, 100 MHz): δ 14.1,
18.8, 19.4, 22.3, 22.7, 27.6, 28.9, 29.0, 29.1, 29.4, 29.5, 29.6, 31.9, 48.2, 67.1, 73.6, 125.8, 126.4, 126.7,
127.1, 128.0, 128.6, 137.4, 138.0, 171.5, 172.4, 196.3, 197.5; HRMS (FAB+): calcd for C26H43NO2S
433.3014 (M+), found 433.2997.