726
N Subhakara Reddy et al.
2.2c Synthesis
of
methyl
2-methoxy-6-(8- 126.6, 129.2, 132.1, 133.6, 135.7, 136.8, 138.8, 146.9,
(2methylphenyl sufonamido) octyl) benzoate (7c): 156.3, 168.2 ppm; ESIMS (m/z): 462.1 (M+H)+.
Using 6 and 2-methylphenylsulphonyl chloride as
starting materials, the title compound 7c was obtained
as a yellow liquid; Yield: 74.4%; IR (neat): νmax 3304,
2.2f Synthesis
of
methyl
2-(8-(2,5-
dichlorophenylsulfonamido)octyl)-6-methoxybenzoate
(7f): Using 6 and 2,5-dichloro phenyl sulphonyl chlo-
ride as starting materials, the title compound 7f was
obtained as a pale yellow liquid; Yield: 60.4%; IR
(neat): νmax 3310, 3085, 3008, 2932, 2856, 1726, 1586,
1456, 1334, 1268, 1164, 1101, 1078, 959, 894 cm−1; 1H
NMR (400 MHz, CDCl3): δ 1.22 (brs, 8H), 1.43–1.56
(m, 4H), 2.52 (t, 2H, J = 7.2 Hz), 2.91–2.96 (m, 2H),
3.82 (s, 3H), 3.91 (s, 3H), 4.96 (brs, 1H), 6.75–6.82
(m, 2H), 7.26–7.29 (m, 1H), 7.46 (brs, 2H), 8.09 (s,
1H) ppm; 13C NMR (100 MHz, CDCl3):δ 26.30, 28.75,
29.06, 29.16, 29.25, 29.30, 29.39, 30.93, 33.34, 43.32,
52.12, 55.82, 108.37, 121.41, 123.41, 129.47, 130.23,
131.09, 132.59, 133.42, 133.46, 138.72, 141.13,
156.22, 168.91 ppm; MF: C23H29Cl2NO5S; Exact Mass:
501.11; ESIMS (m/z): 500.0 (M-H)+. 502.0 (chloro).
3061, 3007, 2932, 2855, 1728, 1588, 1464, 1431, 1318,
1
1270, 1158, 1112, 1073, 959, 755 cm−1; H NMR
(400 MHz, CDCl3): δ 1.18 (brs, 8H), 1.39-1.57 (m,
4H), 2.51 (t, 2H, J = 7.6 Hz), 2.64 (s, 3H), 2.89–2.94
(m, 2H), 3.82 (s, 3H), 3.90 (s, 3H), 4.42 (s, 1H), 6.75–
6.81 (m, 2H), 7.25–7.32 (m, 3H), 7.42-7.46 (m, 1H),
7.95–7.97 (m, 1H) ppm; 13C NMR (100 MHz, CDCl3):
22.0, 26.7, 29.1, 29.2, 29.3, 29.6, 31.3, 36.2, 42.8,
51.5, 55.8, 111.4, 116.0, 120.3, 120,8, 129.7, 130.5,
131.8, 136.6, 136.8, 138.9, 146.9, 156.3, 168.2 ppm;
MF: C24H33NO5S; Exact Mass: 447.21; ESIMS (m/z):
448.1 (M+H)+.
2.2d Synthesis
(methylphenylsulfonamido)octyl)
of
methyl
2-methoxy-6-(8-
benzoate (7d):
Using 6 and para toluene sulphonyl chloride as starting
materials, the title compound 7d was obtained as a light
yellow liquid; Yield: 98%; IR (neat): νmax 3285, 3050,
2931, 2856, 1728, 1589, 1464, 1436, 1322, 1269, 1157,
1104, 1076, 817 cm−1; 1H NMR (400 MHz, CDCl3): δ
1.213 (brs, 8H), 1.39–1.60 (m, 4H), 2.42 (s, 3H), 2.51
(t, 2H, J = 7.6 Hz), 2.88–2.96 (m, 2H) 3.81 (s, 3H),
3.90 (s, 3H), 4.28 (s, 1H), 6.76 (d, 1H, J = 8.4 Hz),
6.80 (d, 1H, J = 7.6 Hz), 7.25–7.31 (m, 3H), 7.73 (d,
2H, J = 8.4Hz) ppm; 13C NMR (100 MHz, CDCl3):
δ 21.43, 26.37, 28.80, 29.06, 29.17, 29.45, 30.94,
33.34, 43.12, 52.10, 55.82, 108.35, 121.41, 123.4,
127.04, 129.6, 130.21, 136.99, 141.15, 143.21, 156.2,
168.9 ppm; MF: C24H33NO5S; Exact Mass: 447.21;
ESIMS (m/z): 446.1 (M-H)+.
2.2g Synthesis
of
methyl
2-methoxy-6-(8-
(phenylmethylsulfonamido) octyl) benzoate (7g):
Using 6 and phenylmethylsulphonyl chloride as start-
ing materials, the title compound 7g was obtained as
a pale yellow liquid; Yield: 26.8%; IR (neat): νmax
3294, 3072, 3034, 2931, 2856, 1727, 1667, 1587, 1461,
1320, 1268, 1147, 1117, 1074, 957 cm−1; H NMR
1
(400 MHz, CDCl3): δ 1.24 (brs, 8H) 1.34–1.56 (m,
4H), 2.53 (t, 2H, J = 7.6 Hz), 2.94–2.99 (m, 2H), 3.82
(s, 3H), 3.90 (s, 3H), 4.00 (s, 3H), 4.25 (s, 2H), 6.76
(d, 1H, J = 8.4 Hz), 6.81 (d, 1H, J = 7.6 Hz), 7.3 (m,
1H), 7.38 (brs, 5H) ppm; 13C NMR (100 MHz, CDCl3):
26.7, 29.1, 29.2, 29.3, 29.6, 31.2, 36.2, 43.2, 51.5, 55.8,
66.0, 111.4, 116.0, 120.3, 125.7, 128.6, 130.8, 133.2,
136.8, 146.9, 156.3, 168.2 ppm; MF: C24H33NO5S;
Exact Mass: 447.21; ESIMS (m/z): 446.1 (M-H)+.
2.2e Synthesis
of
methyl
2-(8-(2,5-
dimethylphenylsufonamido)octyl)-6-methoxybenzoate
(7e): Using 6 and 2,5dimethylphenylsulphonyl chlo-
ride as starting materials, the title compound 7e was
obtained as a yellow liquid; Yield: 74.1%; IR (neat):
νmax 3305, 3066, 3013, 2932, 2856, 1728, 1589, 1464,
1429, 1317, 1268, 1151, 1105, 1073, 967, 896 cm−1;
1H NMR (400 MHz, CDCl3): δ 1.19 (brs, 8H), 1.39–
1.44 (m, 2H), 1.50–1.57 (m, 2H), 2.36 (s, 3H), 2.52 (t,
2H, J = 7.6 Hz), 2.58 (s, 3H), 2.87–2.93 (q, 2H), 3.82
(s, 3H), 3.90 (s, 3H), 4.40 (bs, 1H), 6.75–6.81 (m, 2H),
7.17–7.19 (m, 1H), 7.23–7.288 (m, 2H), 7.78 (s, 1H)
ppm; MF: C25H35NO5S; Exact Mass: 461.22; 13C NMR
(100 MHz, CDCl3): 21.3, 22.0, 26.7, 29.1, 29.2, 29.3,
29.6, 31.2, 36.2, 42.8, 51.5, 55.8, 111.4, 116.0, 120.3,
2.2h Synthesis
of
methyl
2-methoxy-6-(8-
(naphthalene-2-sulfonamido) octyl) benzoate (7h):
Using 6 and naphthalene-2-sulphonyl chloride as start-
ing materials, the title compound 7h was obtained as
a light yellow liquid; Yield: 82.9%; IR (neat): 3286,
3056, 2929, 2855, 1726, 1587, 1511, 1461, 1323, 1268,
1156, 1111, 1074, 960, 903 cm−1; 1H NMR (400 MHz,
CDCl3): δ 1.187 (broad singlet, 8H), 1.42–1.52 (m,
4H), 2.49 (t, 2H, J = 7.6 Hz), 2.95–2.99 (m, 2H), 3.82
(s, 3H), 3.89 (s, 3H), 4.45 (brs, 1H), 6.75–6.80 (m, 2H),
7.24–7.28 (m, 1H), 7.59–7.66 (m, 2H), 7.82–8.02 (m,
4H), 8.44 (s, 1H) ppm; MF: C27H33NO5S; Exact Mass:
483.21; 13C NMR (100 MHz, CDCl3): 26.7, 29.1, 29.2,