34
4 Experimental Data
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(51.4 mg, 77%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.63 (d, J = 7.7 Hz, 1H
Ar
), 7.34–7.08 (m,
9H
Ar
), 6.55 (d, J = 3.3 Hz, 1H
13
), 4.97–4.92 (m, 1H
1
), 3.58–3.39 (m, 2H
6
), 3.28–
3.20 (m, 1H
9
), 2.88–2.79 (m, 1H
9
), 2.65–2.52 (m, 3H
Alk
), 2.43–2.31 (m, 1H
Alk
),
1.87–1.66 (m, 4H
Alk
), 1.51–1.40 (m, 1H
Alk
) ppm;
13
C NMR (175 MHz, CDCl3):
δ = 167.8 (C
2
), 140.8 (C
Ar
), 136.1 (C
Ar
), 128.7 (C
Ar
), 128.6 (2CH
Ar
), 128.6
(2CH
Ar
), 126.3 (CH
Ar
), 126.2 (CH
Ar
), 121.8 (CH
Ar
), 121.2 (CH
Ar
), 119.8 (CH
Ar
),
109.1 (CH
Ar
), 102.3 (CH
Ar
), 56.2 (CH
1
), 46.4 (CH2
6
), 46.2 (CH2
9
), 33.8 (CH2
Alk
),
31.9 (CH2
Alk
), 26.2 (CH2
Alk
), 24.0 (CH2
Alk
) ppm; IR (neat):
= 3026, 2969,
2875, 1645, 1456, 1400, 1308, 1192, 700 cm
-1
; HRMS (ESI): m/z calculated for
[M+Na]
+
(C22H24N2ONa) 355.1781, found 355.1780.
2.1b N-Methyl-4-nitro-N-(1-oxo-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)benzenesulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(82.3 mg, 82%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.30 (d, J = 9.0 Hz, 2H
25,27
), 7.82 (d, J =
9.0 Hz, 2H
24,28
), 7.35–7.29 (m, 2H
16,18
), 7.27–7.21 (m, 1H
17
), 7.15–7.10 (m,
2H
15,19
), 4.63 (apt, J = 7.5 Hz, 1H
1
), 3.64–3.57 (m, 1H
6
), 3.41–3.19 (m, 3H
6,9
),
3.02 (s, 3H
11
), 2.67–2.50 (m, 2H
13
), 2.18–2.07 (m, 1H
Alk
), 1.98–1.80 (m, 4H
Alk
),
1.65–1.55 (m, 1H
Alk
) ppm;
13
C NMR (100 MHz, CDCl3): δ = 167.7 (C
2
), 150.1
(C
26
), 144.8 (C
Ar
), 140.4 (C
Ar
), 128.8 (2CH
Ar
), 128.6 (2CH
Ar
), 128.5 (2CH
Ar
),
126.7 (CH
17
), 124.3 (2CH
Ar
), 56.4 (CH
1
), 46.5 (CH2
6
), 46.1 (CH2
6
), 32.1(CH2
Alk
),
30.8 (CH3
11
), 30.3 (CH2
Alk
), 26.3 (CH2
Alk
), 24.2 (CH2
Alk
) ppm; IR (neat):
=
3103, 3063, 2974, 2876, 1642, 1529, 1448, 1349, 1162, 855, 699, 608 cm
-1
;
HRMS (ESI): m/z calculated for [M+Na]
+
(C21H25N3O5SNa) 454.1407, found
454.1411.
4 Experimental Data
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(51.4 mg, 77%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.63 (d, J = 7.7 Hz, 1H
Ar
), 7.34–7.08 (m,
9H
Ar
), 6.55 (d, J = 3.3 Hz, 1H
13
), 4.97–4.92 (m, 1H
1
), 3.58–3.39 (m, 2H
6
), 3.28–
3.20 (m, 1H
9
), 2.88–2.79 (m, 1H
9
), 2.65–2.52 (m, 3H
Alk
), 2.43–2.31 (m, 1H
Alk
),
1.87–1.66 (m, 4H
Alk
), 1.51–1.40 (m, 1H
Alk
) ppm;
13
C NMR (175 MHz, CDCl3):
δ = 167.8 (C
2
), 140.8 (C
Ar
), 136.1 (C
Ar
), 128.7 (C
Ar
), 128.6 (2CH
Ar
), 128.6
(2CH
Ar
), 126.3 (CH
Ar
), 126.2 (CH
Ar
), 121.8 (CH
Ar
), 121.2 (CH
Ar
), 119.8 (CH
Ar
),
109.1 (CH
Ar
), 102.3 (CH
Ar
), 56.2 (CH
1
), 46.4 (CH2
6
), 46.2 (CH2
9
), 33.8 (CH2
Alk
),
31.9 (CH2
Alk
), 26.2 (CH2
Alk
), 24.0 (CH2
Alk
) ppm; IR (neat):
= 3026, 2969,
2875, 1645, 1456, 1400, 1308, 1192, 700 cm
-1
; HRMS (ESI): m/z calculated for
[M+Na]
+
(C22H24N2ONa) 355.1781, found 355.1780.
2.1b N-Methyl-4-nitro-N-(1-oxo-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)benzenesulfonamide
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(82.3 mg, 82%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.30 (d, J = 9.0 Hz, 2H
25,27
), 7.82 (d, J =
9.0 Hz, 2H
24,28
), 7.35–7.29 (m, 2H
16,18
), 7.27–7.21 (m, 1H
17
), 7.15–7.10 (m,
2H
15,19
), 4.63 (apt, J = 7.5 Hz, 1H
1
), 3.64–3.57 (m, 1H
6
), 3.41–3.19 (m, 3H
6,9
),
3.02 (s, 3H
11
), 2.67–2.50 (m, 2H
13
), 2.18–2.07 (m, 1H
Alk
), 1.98–1.80 (m, 4H
Alk
),
1.65–1.55 (m, 1H
Alk
) ppm;
13
C NMR (100 MHz, CDCl3): δ = 167.7 (C
2
), 150.1
(C
26
), 144.8 (C
Ar
), 140.4 (C
Ar
), 128.8 (2CH
Ar
), 128.6 (2CH
Ar
), 128.5 (2CH
Ar
),
126.7 (CH
17
), 124.3 (2CH
Ar
), 56.4 (CH
1
), 46.5 (CH2
6
), 46.1 (CH2
6
), 32.1(CH2
Alk
),
30.8 (CH3
11
), 30.3 (CH2
Alk
), 26.3 (CH2
Alk
), 24.2 (CH2
Alk
) ppm; IR (neat):
=
3103, 3063, 2974, 2876, 1642, 1529, 1448, 1349, 1162, 855, 699, 608 cm
-1
;
HRMS (ESI): m/z calculated for [M+Na]
+
(C21H25N3O5SNa) 454.1407, found
454.1411.