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The mixture was allowed to warm to room temperature and was
stirred overnight under nitrogen atmosphere. The reaction was di-
luted with EtOAc (20 mL) and washed with 1 n HCl (20 mL), satu-
C H N NaO S: 681.3180, found: 681.3158; Anal. calcd for
35
50
2
8
C H N O S: C 63.80, H 7.66, N 4.25, found: C 63.33, H 7.54, N 4.20.
35
50
2
8
rated NaHCO (20 mL), and brine (20 mL). The organic layer was
Compound 5e: White solid (69 mg, 80% yield): mp: 133–1358C;
3
1
dried over Na SO , filtered, and concentrated. Purification by flash
H NMR (400 MHz, CDCl ): d=7.09 (d, J=7.1 Hz, 1H), 6.84 (dd, J=
2
4
3
column chromatography gave the pure compound.
15.1, 5.4 Hz, 1H), 6.51 (d, J=15.1 Hz, 1H), 6.23 (brs, 1H), 4.69 (m,
1
H), 4.50 (m, 1H), 2.95 (s, 3H), 2.27 (m, 1H), 1.63 (m, 28H), 1.00–
13
Compound 5a: White solid (42 mg, 49% yield): mp: 108–1108C;
0.82 ppm (m, 12H); C NMR (101 MHz, CDCl ): d=175.2, 171.9,
3
1
H NMR (400 MHz, CDCl ), d=7.87 (d, J=8.0 Hz, 2H), 7.64 (t, J=
147.6, 129.3, 110.6, 106.9, 51.7, 47.9, 43.8, 42.8, 42.7, 40.5, 36.9,
33.1, 27.0, 24.9, 24.7, 22.9, 22.8, 22.2, 21.9 ppm; IR (NaCl): n˜ =1641
(C=O), 1539 (C=C), 1312 (S=O asymmetric), 1137 (S=O symmetric),
3
7
.2 Hz, 1H), 7.55 (t, J=8.0 Hz, 2H), 7.27 (t, J=7.2 Hz, 2H), 7.19 (t,
J=7.0 Hz, 1H), 7.08 (d, J=7.6 Hz, 2H), 7.00 (d, J=8.4 Hz, 1H), 6.90
dd, J=15.0 Hz and 5.2 Hz, 1H), 6.44 (d, J=15.0 Hz, 1H), 6.10 (d,
J=8.0 Hz, 1H), 4.64 (m, 1H), 4.43 (m, 1H), 2.58 (m, 2H), 2.22 (m,
À1
+
(
832 cm (OÀO); HRMS-ESI: m/z [M+Na] calcd for C H N NaO S:
31
50
2
8
633.3186, found: 633.3178; Anal. calcd for C H N O S·0.15H O: C
31
50
2
8
2
1
6
1
1
2
H), 1.45–2.05 (m, 27H), 0.89 (d, J=6.0 Hz, 3H), 0.85 ppm (d, J=
60.69, H 8.28, N 4.57, found: C 60.34, H 8.18, N 4.55.
1
3
.0 Hz, 3H); C NMR (101 MHz, CDCl ), d=175.2, 171.7, 145.4,
3
40.3, 140.1, 133.6, 130.9, 129.4, 128.6, 128.4, 127.7, 126.3, 110.6,
06.9, 51.7, 49.1, 43.7, 36.9, 35.5, 33.1, 31.8, 27.0, 24.8, 22.8,
Compound 5 f: White solid (96 mg, 52% yield): mp: 109–1118C;
1
H NMR (400 MHz, CDCl ): d=7.81–7.75 (dd, J=8.0, 0,8 Hz, 2H),
3
2.2 ppm; IR (NaCl): n˜ =1640 (C=O), 1539 (C=C), 1321 (S=O asym-
7.51 (m, 1H), 7.47 (t, J=8 Hz, 2H), 7.22–7.16 (m, 2H), 7.11 (t, J=
7.2 Hz, 1H), 7.01 (d, J=7.2 Hz, 2H), 6.82 (dd, J=15.1, 5.3 Hz, 1H),
6.69 (brs, 1H), 6.35 (dd, J=15.1, 1.4 Hz, 1H), 5.90 (brs, 1H), 4.58
(m, 1H), 4.33 (m, 1H), 2.60–2.45 (m, 2H), 2.06–1.32 (m, 30H), 0.82
À1
metric), 1308 (S=O asymmetric), 1149 (S=O symmetric), 844 cm
+
(
OÀO); HRMS-ESI: m/z [M+H] calcd for C H N O S: 721.3517,
40
53
2
8
found: 721.3526; Anal. calcd for C H N O S·0.15H O: C 66.39, H
40
53
2
8
2
1
3
7
.30, N 3.87, found: C 66.00, H 7.42, N 3.74.
(dd, J=6.0 Hz, 3H), 0.78 ppm (d, J=6.0 Hz, 3H);
C NMR
(
101 MHz, CDCl ): d=181.8, 171.6, 145.3, 140.3, 140.0, 133.6, 130.9,
3
Compound 5b: White solid (63 mg, 72% yield): mp: 115–1208C;
129.4, 128.7, 128.4, 127.7, 126.4, 110.5, 107.5, 51.8, 49.2, 43.0, 40.3,
36.9, 35.7, 34.0, 33.1, 31.8, 27.0, 24.8, 22.8, 22.1 ppm; IR (NaCl): n˜ =
1639 (C=O), 1546 (C=C), 1320 (S=O asymmetric), 1308 (S=O asym-
1
H NMR (400 MHz, CDCl ): d=7.81 (d, J=7.6 Hz, 2H), 7.63 (t, J=
3
7
6
2
4
2
.6 Hz, 1H), 7.54 (t, J=7.6 Hz, 2H), 7.26–7.17 (m, 3H), 7.11 (d, J=
.4 Hz, 2H), 7.00 (d, J=8.4 Hz, 1H), 6.94 (dd, J=15.0 Hz, 5.2 Hz,
H), 6.35 (dd, J=15.0, 1.2 Hz, 1H), 6.00 (brs, 1H), 4.96 (m, 1H),
.39 (m, 1H), 2.90 (d, J=7.2 Hz, 2H), 2.14 (m, 1H), 2.09–1.39 (m,
À1
metric), 1149 (S=O symmetric), 847 cm (OÀO); HRMS-ESI: m/z
+
[M+H] calcd for C H N O S: 735.3674, found: 735.3671; Anal.
41
55
2
8
calcd for C H N O S·0.5H O: C 66.19, H 7.47, N 3.77, found: C
41
54
2
8
2
13
5H), 0.87 (d, J=6.2 Hz, 3H), 0.83 ppm (d, J=6.2 Hz, 3H); C NMR
65.84, H 7.27, N 3.78.
(
101 MHz, CDCl ): d=174.9, 171.6, 144.8, 140.0, 135.7, 133.5, 131.0,
3
1
4
29.3, 129.3, 128.7, 127.6, 127.1, 110.6, 106.9, 51.6, 50.4, 43.6, 40.3,
0.0, 36.9, 33.1, 27.0, 24.8, 22.8, 22.1 ppm; IR (NaCl): n˜ =1643 (C=
Compound 5i: White solid (42 mg, 56% yield): mp: 84–878C;
1
H NMR (400 MHz, CDCl ): d=7.87 (d, J=7.6 Hz, 2H), 7.64 (t, J=
3
O), 1544 (C=C), 1320 (S=O asymmetric), 1308 (S=O asymmetric),
7.3 Hz, 1H), 7.55 (t, J=7.6 Hz, 2H), 7.30–7.23 (m, 2H), 7.19 (t, J=
7.2 Hz, 1H), 7.08 (d, J=7.2 Hz, 2H), 7.00 (d, J=8.3 Hz, 1H), 6.90
(dd, J=15.1, 5.3 Hz, 1H), 6.44 (d, J=15.1 Hz, 1H), 6.12 (d, J=
8.0 Hz, 1H), 4.63 (m, 1H), 4.44 (m, 1H), 2.66–2.51 (m, 2H), 2.40–
À1
+
1
148 (S=O symmetric), 847 cm (OÀO); HRMS-ESI: m/z [M+Na]
calcd for C H N NaO S: 729.3180, found: 729.3159; Anal. calcd for
3
9
50
2
8
C H N O S: C 66.26, H 7.14, N 3.96, found: C 66.48, H 6.89, N 3.51.
3
9
50
2
8
2
.16 (m, 3H), 1.98–1.36 (m, 23H), 0.89 (d, J=6.1 Hz, 3H), 0.85 ppm
13
Compound 5c: White solid (55 mg, 83% yield): mp: 185–1868C;
(d, J=6.1 Hz, 3H); C NMR (101 MHz, CDCl ): d=175.1, 171.7,
3
1
H NMR (400 MHz, CDCl ): d=7.85 (d, J=7.6 Hz, 2H), 7.66 (t, J=
145.4, 140.3, 140.1, 133.6, 130.9, 129.4, 128.6, 128.4, 127.7, 126.3,
108.5, 107.0, 82.5, 51.7, 49.1, 43.7, 40.4, 35.5, 31.8, 29.7, 25.3, 24.8,
22.8, 22.2 ppm; IR (NaCl): n˜ =1652 (C=O), 1640 (C=O), 1539 (C=C),
1321 (S=O asymmetric), 1308 (S=O asymmetric), 1149 (S=O sym-
3
7
6
6
1
2
.2 Hz, 1H), 7.57 (t, J=7.6 Hz, 2H), 7.30–7.15 (m, 6H), 7.12 (d, J=
.8 Hz, 2H), 7.06 (d, J=7.2 Hz, 2H), 6.78 (dd, J=15.2, 4.8 Hz, 1H),
.52 (d, J=8.4 Hz, 1H), 6.27 (d, J=7.6 Hz, 1H), 6.02 (d, J=15.2 Hz,
H), 4.70–4.55 (m, 2H), 3.00 (d, J=7.2 Hz, 2H), 2.62–2.47 (m, 2H),
À1
+
metric), 849 cm
(OÀO); HRMS-ESI: m/z [M+H] calcd for
13
.19 (m, 1H), 2.07–1.39 ppm (m, 24H); C NMR (101 MHz, CDCl3):
C H N O S: 669.3204, found: 669.3201; Anal. calcd for
36 49 2 8
d=174.8, 170.6, 145.2, 140.2, 136.1, 133.5, 130.6, 129.3, 129.1,
C H N O S·0.75H O: C 63.36, H 7.33, N 4.11, found: C 63.36, H
36 48 2 8 2
1
3
1
8
7
6
28.8, 128.6, 128.3, 127.7, 127.3, 126.3, 110.6, 106.9, 54.6, 49.1, 43.6,
8.2, 36.9, 35.5, 33.1, 31.7, 27.0 ppm; IR (NaCl): n˜ =1640 (C=O),
539 (C=C), 1311 (S=O asymmetric), 1134 (S=O symmetric),
7.05, N 4.59.
Compound 6: White solid (77 mg, 51% yield): mp: 107–1108C;
À1
+
1
34 cm (OÀO); HRMS-ESI: m/z [M+Na] calcd for C H N NaO S:
H NMR (400 MHz, CDCl ): d=7.85 (d, J=7.5 Hz, 2H), 7.62 (t, J=
43
50
2
8
3
77.3180, found: 777.3147; Anal. calcd for C H N O S·1.5H O: C
7.5 Hz, 1H), 7.53 (t, J=7.5 Hz, 2H), 7.25 (t, J=7.1 Hz, 2H), 7.18 (t,
J=7.1 Hz, 1H), 7.07 (d, J=7.1 Hz, 2H), 6.88 (m, 3H), 6.41 (d, J=
43
50
2
8
2
6.04, H 6.85, N 3.58, found: C 66.03, H 7.23, N 3.86.
1
5.0 Hz, 1H), 5.97 (d, J=7.9 Hz, 1H), 4.61 (m, 1H), 4.39 (m, 1H),
Compound 5d: White solid (60 mg, 52% yield): mp: 118–1218C;
2.64–2.49 (m, 2H), 2.11 (m, 1H), 2.04–1.40 (m, 27H), 0.88 (d, J=
6.1 Hz, 3H), 0.83 ppm (d, J=6.1 Hz, 3H); C NMR (101 MHz, CDCl3):
1
13
H NMR (400 MHz, CDCl ): d=7.27 (d, J=7.5 Hz, 3H), 7.20 (dd, J=
3
1
1
4
2
3
1
3
1
2.3, 7.5 Hz, 2H), 7.11 (d, J=7.5 Hz, 2H), 6.84 (dd, J=15.0, 5.1 Hz,
H), 6.50 (d, J=15.0 Hz, 1H), 6.22 (d, J=5.9 Hz, 1H), 4.62 (m, 1H),
.51 (m, 1H), 3.14 (brs, 2H), 2.94 (s, 3H), 2.61 (m, 2H), 2.25 (m, 1H),
.06–1.41 (m, 31H), 0.96 (d, J=5.2 Hz, 3H), 0.92 ppm (d, J=5.2 Hz,
d=175.39, 171.66, 145.35, 140.31, 140.11, 133.51, 130.91, 129.34,
128.61, 128.37, 127.64, 126.31, 111.59, 107.58, 51.69, 49.09, 43.36,
40.28, 36.75, 36.35, 35.55, 34.80, 34.77, 33.45, 33.40, 31.80, 29.69,
27.03, 26.88, 26.85, 26.45, 24.83, 22.74, 22.18 ppm; IR (NaCl): n˜ =
1640 (C=O), 1539 (C=C), 1321 (S=O asymmetric), 1308 (S=O asym-
1
3
H); C NMR (101 MHz, CDCl ): d=175.3, 172.0, 147.0, 140.3,
3
À1
29.8, 128.7, 128.4, 126.4, 110.6, 106.9, 51.7, 49.2, 43.8, 42.8, 40.4,
6.9, 35.4, 33.1, 31.8, 29.7, 27.0, 24.9, 23.0, 22.1 ppm; IR (NaCl): n˜ =
640 (C=O), 1539 (C=C), 1310 (S=O asymmetric), 1134 (S=O sym-
metric), 1147 (S=O symmetric), 844 cm (OÀO); HRMS-ESI: m/z
+
[M+H] calcd for C H N O S: 705.3568, found 705.3566; Anal.
40
53
2
7
calcd for C H N O S: C 68.15, H 7.45, N 3.97, found: C 67.84, H
40 52 2 7
7.64, N 3.87.
À1
+
metric), 834 cm
(OÀO); HRMS-ESI: m/z [M+Na] calcd for
ꢀ
2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ChemMedChem 2013, 8, 1528 – 1536 1534