48
4 Experimental Data
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:3) yielded the product
(60.0 mg, 72%) as a pale yellow solid.
1
H NMR (400 MHz, CDCl3): δ = 8.25 (d, J = 9.0 Hz, 2H
25,27
), 7.78 (d, J =
9.0 Hz, 2H
24,28
), 7.27–7.21 (m, 3H
Ar
), 7.14–7.10 (m, 2H
Ar
), 4.94 (dd, J = 9.2, 6.2
Hz, 1H
1
), 3.65–3.57 (m, 1H
6
), 3.33–3.12 (m, 3H
6,9
), 3.13 (s, 3H
11
), 2.87–2.79 (m,
1H
13
), 2.71 (dd, J = 13.3, 6.2 Hz, 1H
13
), 1.90–1.64 (m, 4H
Alk
) ppm;
13
C NMR (100
MHz, CDCl3): δ = 167.7 (C
2
), 150.0 (C
26
), 144.9 (C
Ar
), 136.2 (C
Ar
), 129.3
(2CH
Ar
), 128.9 (2CH
Ar
), 128.4 (2CH
Ar
), 127.3 (CH
23
), 124.3 (CH
Ar
), 58.3 (CH
1
),
46.5 (CH2
6
), 45.8 (CH2
9
), 36.0 (CH2
3
), 31.0 (CH3
19
), 26.1 (CH2
7
), 24.2 (CH2
8
)
ppm; IR (neat):
= 3104, 3063, 3029, 2876, 1640, 1528, 1447, 1347, 1162, 942,
853, 738, 699, 609 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C20H23N3O5SNa) 440.1244, found 440.1251.
2.1u N,4-Dimethyl-N-(1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)benzene-sulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(37.1 mg, 57%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.64 (d, J = 8.2 Hz, 2H
17,21
), 7.28 (d, J =
8.2 Hz, 2H
18,20
), 4.57 (dd, J = 8.4, 6.5 Hz, 1H
1
), 3.86–3.79 (m, 1H
6
), 3.50–3.37
(m, 2H
6,9
), 3.34–3.26 (m, 1H
9
), 2.92 (s, 3H
11
), 2.42 (s, 3H
22
), 2.00–1.92 (m, 2H
7
),
1.88–1.75 (m, 3H
2x8,3
), 1.39–1.28 (m, 1H
3
), 0.84 (t, J = 7.5 Hz, 3H
13
) ppm;
13
C
NMR (125 MHz, CDCl3): δ = 168.4 (C
2
), 143.5 (C
14
), 136.5 (C
19
), 129.7
(2CH
17,21
), 127.3 (2CH
18,20
), 58.5 (CH
1
), 46.7 (CH
6
), 46.0 (CH
9
), 30.3 (CH3
11
),
26.3 (CH2
Alk
), 24.3 (CH2
Alk
), 21.7 (CH2
Alk
), 21.6 (CH3
22
), 10.8 (CH3
13
) ppm; IR
(neat):
= 2969, 2877, 1642, 1444, 1336, 1163, 1151, 1088, 955, 812, 714, 652
cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C16H24N2O3SNa) 347.1400,
found 347.1401.
4 Experimental Data
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:3) yielded the product
(60.0 mg, 72%) as a pale yellow solid.
1
H NMR (400 MHz, CDCl3): δ = 8.25 (d, J = 9.0 Hz, 2H
25,27
), 7.78 (d, J =
9.0 Hz, 2H
24,28
), 7.27–7.21 (m, 3H
Ar
), 7.14–7.10 (m, 2H
Ar
), 4.94 (dd, J = 9.2, 6.2
Hz, 1H
1
), 3.65–3.57 (m, 1H
6
), 3.33–3.12 (m, 3H
6,9
), 3.13 (s, 3H
11
), 2.87–2.79 (m,
1H
13
), 2.71 (dd, J = 13.3, 6.2 Hz, 1H
13
), 1.90–1.64 (m, 4H
Alk
) ppm;
13
C NMR (100
MHz, CDCl3): δ = 167.7 (C
2
), 150.0 (C
26
), 144.9 (C
Ar
), 136.2 (C
Ar
), 129.3
(2CH
Ar
), 128.9 (2CH
Ar
), 128.4 (2CH
Ar
), 127.3 (CH
23
), 124.3 (CH
Ar
), 58.3 (CH
1
),
46.5 (CH2
6
), 45.8 (CH2
9
), 36.0 (CH2
3
), 31.0 (CH3
19
), 26.1 (CH2
7
), 24.2 (CH2
8
)
ppm; IR (neat):
= 3104, 3063, 3029, 2876, 1640, 1528, 1447, 1347, 1162, 942,
853, 738, 699, 609 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C20H23N3O5SNa) 440.1244, found 440.1251.
2.1u N,4-Dimethyl-N-(1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)benzene-sulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(37.1 mg, 57%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.64 (d, J = 8.2 Hz, 2H
17,21
), 7.28 (d, J =
8.2 Hz, 2H
18,20
), 4.57 (dd, J = 8.4, 6.5 Hz, 1H
1
), 3.86–3.79 (m, 1H
6
), 3.50–3.37
(m, 2H
6,9
), 3.34–3.26 (m, 1H
9
), 2.92 (s, 3H
11
), 2.42 (s, 3H
22
), 2.00–1.92 (m, 2H
7
),
1.88–1.75 (m, 3H
2x8,3
), 1.39–1.28 (m, 1H
3
), 0.84 (t, J = 7.5 Hz, 3H
13
) ppm;
13
C
NMR (125 MHz, CDCl3): δ = 168.4 (C
2
), 143.5 (C
14
), 136.5 (C
19
), 129.7
(2CH
17,21
), 127.3 (2CH
18,20
), 58.5 (CH
1
), 46.7 (CH
6
), 46.0 (CH
9
), 30.3 (CH3
11
),
26.3 (CH2
Alk
), 24.3 (CH2
Alk
), 21.7 (CH2
Alk
), 21.6 (CH3
22
), 10.8 (CH3
13
) ppm; IR
(neat):
= 2969, 2877, 1642, 1444, 1336, 1163, 1151, 1088, 955, 812, 714, 652
cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C16H24N2O3SNa) 347.1400,
found 347.1401.