40
4 Experimental Data
2.1i Methyl N-(1-oxo-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)-N-tosylglycinate
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:2) yielded the product
(58.0 mg, 63%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.66 (d, J = 8.3 Hz, 2H
Ar
), 7.32–7.16 (m,
5H
Ar
), 7.04 (d, J = 8.3 Hz, 2H
Ar
), 4.39 (d, J = 18.3 Hz, 1H
11
), 3.39–3.34 (m, 1H
1
),
4.17 (d, J = 18.3 Hz, 1H
11
), 3.71 (s, 3H
12
), 3.54–3.45 (m, 1H
6
), 3.38–3.22 (m, 2H
9
),
3.02–2.93 (m, 1H
6
), 2.66–2.57 (m, 1H
Alk
), 2.53–2.44 (m, 1H
Alk
), 2.43 (s, 3H
29
),
2.12–2.01 (m, 1H
Alk
), 1.90–1.74 (m, 4H
Alk
), 1.62–1.51 (m, 1H
Alk
) ppm;
13
C NMR
(100 MHz, CDCl3): δ = 170.5 (C
4
), 167.4 (C
2
), 144.0 (C
Ar
), 140.7 (C
Ar
), 137.0
(C
Ar
), 129.8 (2CH
Ar
), 128.6 (2CH
Ar
), 128.6 (2CH
Ar
), 127.8 (2CH
Ar
), 126.4 (CH
17
),
55.7 (CH
1
), 52.3 (CH
12
), 46.2 (CH2
6
), 46.1 (CH2
9
), 45.3 (CH2
11
), 31.9 (CH2
Alk
),
30.9 (CH2
Alk
), 26.2 (CH2
Alk
), 24.2 (CH2
Alk
), 21.7 (CH3
29
) ppm; IR (neat):
=
2951, 2876, 2251, 1756, 1638, 1598, 1447, 1341, 1206, 1156, 1093, 909, 813, 727,
700, 654 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C24H30N2O5SNa)
481.1768, found 481.1758.