46
4 Experimental Data
1
H NMR (400 MHz, CDCl3): δ = 7.65 (d, J = 8.4 Hz, 2H
24,28
), 7.30 (d, J =
8.4 Hz, 2H
25,27
), 4.63 (dd, J = 8.8, 6.1 Hz, 1H
1
), 3.87–3.78 (m, 1H
6
), 3.52–3.27
(m, 5H
6,9,10
), 2.89 (s, 3H
11
), 2.42 (s, 3H
29
), 2.02–1.92 (m, 2H
Alk
), 1.88–1.60 (m,
5H
Alk
), 1.40–1.21 (m, 3H
Alk
) ppm;
13
C NMR (100 MHz, CDCl3): δ = 167.9 (C
2
),
143.7 (C
21
), 136.3 (C
26
), 129.8 (2CH
24,28
), 127.3 (2CH
25,27
), 57.0 (CH
1
), 46.8
(CH2
6
), 46.1 (CH2
9
), 44.6 (CH2
10
), 32.2 (CH2
10
), 30.4 (CH3
11
), 27.4 (CH2
Alk
), 26.3
(CH2
Alk
), 24.3 (CH2
Alk
), 23.6 (CH2
Alk
), 21.7 (CH3
29
) ppm; IR (neat):
= 2951,
2873, 1640, 1441, 1334, 1154, 1088, 929, 912, 815, 713, 652 cm
-1
; HRMS (ESI):
m/z calculated for [M+Na]
+
(C18H27ClN2O3SNa) 409.1323, found 409.1330.
2.1r N,4-Dimethyl-N-(1-oxo-1-(pyrrolidin-1-yl)undec-10-en-2-yl)benzene-sulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:19-2:3) yielded the product
(39.6 mg, 47%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.64 (d, J = 8.3 Hz, 2H
24,28
), 7.28 (d, J =
8.3 Hz, 2H
25,27
), 5.86–5.75 (m, 1H
15
), 5.03–4.91 (m, 2H
16
), 4.62 (dd, J = 8.0, 6.0
Hz, 1H
1
), 3.86–3.78 (m, 1H
6
), 3.66 (s, 3H
17
), 3.50–3.25 (m, 3H
6,9
), 2.91 (s, 3H
11
),
2.42 (s, 3H
29
), 2.07–1.92 (m, 2H
Alk
), 1.88–1.69 (m, 3H
Alk
), 1.40–1.12 (m, 11H
Alk
)
ppm;
13
C NMR (175 MHz, CDCl3): δ = 168.5 (C
2
), 143.5 (C
21
), 139.2 (CH
15
),
136.5 (C
26
), 129.7 (2CH
24,28
), 127.3 (2CH
25,27
), 114.4 (CH2
16
), 57.0 (CH
1
), 46.7
(CH2
6
), 46.0 (CH2
9
), 33.9 (CH2
14
), 30.4 (CH3
11
), 29.4 (CH2
Alk
), 29.3 (CH2
Alk
), 29.1
(CH2
Alk
), 29.0 (CH2
Alk
), 28.3 (CH2
Alk
), 26.3 (CH2
Alk
), 26.2 (CH2
Alk
), 24.3 (CH2
Alk
),
21.7 (CH3
29
) ppm; IR (neat):
= 3070, 2925, 2855, 1643, 1441, 1338, 1160,
1088, 910, 815, 713, 652 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C23H36N2O3SNa) 443.2339, found 443.2336.
4 Experimental Data
1
H NMR (400 MHz, CDCl3): δ = 7.65 (d, J = 8.4 Hz, 2H
24,28
), 7.30 (d, J =
8.4 Hz, 2H
25,27
), 4.63 (dd, J = 8.8, 6.1 Hz, 1H
1
), 3.87–3.78 (m, 1H
6
), 3.52–3.27
(m, 5H
6,9,10
), 2.89 (s, 3H
11
), 2.42 (s, 3H
29
), 2.02–1.92 (m, 2H
Alk
), 1.88–1.60 (m,
5H
Alk
), 1.40–1.21 (m, 3H
Alk
) ppm;
13
C NMR (100 MHz, CDCl3): δ = 167.9 (C
2
),
143.7 (C
21
), 136.3 (C
26
), 129.8 (2CH
24,28
), 127.3 (2CH
25,27
), 57.0 (CH
1
), 46.8
(CH2
6
), 46.1 (CH2
9
), 44.6 (CH2
10
), 32.2 (CH2
10
), 30.4 (CH3
11
), 27.4 (CH2
Alk
), 26.3
(CH2
Alk
), 24.3 (CH2
Alk
), 23.6 (CH2
Alk
), 21.7 (CH3
29
) ppm; IR (neat):
= 2951,
2873, 1640, 1441, 1334, 1154, 1088, 929, 912, 815, 713, 652 cm
-1
; HRMS (ESI):
m/z calculated for [M+Na]
+
(C18H27ClN2O3SNa) 409.1323, found 409.1330.
2.1r N,4-Dimethyl-N-(1-oxo-1-(pyrrolidin-1-yl)undec-10-en-2-yl)benzene-sulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:19-2:3) yielded the product
(39.6 mg, 47%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.64 (d, J = 8.3 Hz, 2H
24,28
), 7.28 (d, J =
8.3 Hz, 2H
25,27
), 5.86–5.75 (m, 1H
15
), 5.03–4.91 (m, 2H
16
), 4.62 (dd, J = 8.0, 6.0
Hz, 1H
1
), 3.86–3.78 (m, 1H
6
), 3.66 (s, 3H
17
), 3.50–3.25 (m, 3H
6,9
), 2.91 (s, 3H
11
),
2.42 (s, 3H
29
), 2.07–1.92 (m, 2H
Alk
), 1.88–1.69 (m, 3H
Alk
), 1.40–1.12 (m, 11H
Alk
)
ppm;
13
C NMR (175 MHz, CDCl3): δ = 168.5 (C
2
), 143.5 (C
21
), 139.2 (CH
15
),
136.5 (C
26
), 129.7 (2CH
24,28
), 127.3 (2CH
25,27
), 114.4 (CH2
16
), 57.0 (CH
1
), 46.7
(CH2
6
), 46.0 (CH2
9
), 33.9 (CH2
14
), 30.4 (CH3
11
), 29.4 (CH2
Alk
), 29.3 (CH2
Alk
), 29.1
(CH2
Alk
), 29.0 (CH2
Alk
), 28.3 (CH2
Alk
), 26.3 (CH2
Alk
), 26.2 (CH2
Alk
), 24.3 (CH2
Alk
),
21.7 (CH3
29
) ppm; IR (neat):
= 3070, 2925, 2855, 1643, 1441, 1338, 1160,
1088, 910, 815, 713, 652 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C23H36N2O3SNa) 443.2339, found 443.2336.
