Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
(1S, 3R, 4R, 5R)-1, 3, 4-tri-(acetyl p-coumaroyl) quinide, (101)
15
O
35 O
38
16
10
11
12
14 13
O
7 O
O
1 6 5
8 O 2 3 4
9
O O
O
O
17 26
19
18 27 28
29
20
30
25 21 34
31
24 22
23
O
O
36
39
33
O
32
O
37
40
To a suspension of quinic acid (0.200 g, 1.0407 mmol) and N,N-
(dimethylamino)pyridine (0.006 g, 0.052 mmol) in dichloromethane (6 ml) were
added triethylamine (0.6 ml) and acetyl p-coumaroyl chloride (0.934 g, 4.163
mmol) at room temperature. The reaction mixture was stirred for 18 hours at room
temperature. The reaction solution was extracted with dichloromethane (50 ml)
and 2M HCl (10 ml). The organic phase was dried with MgSO 4 , filtered and the
solvent was removed under reduced pressure to give the title compound (1S, 3R,
4R, 5R)-1, 3, 4-tri-(acetyl p-coumaroyl) quinide (101) as white powder (0.560 g,
73%). Rf 0.88 [chloroform: acetone (8:2)]; ν max (KBr)/cm -1 : 1785 (C=O), 1631
(C Ar =C Ar ), 1158 (C-O); δ H (400 MHz, CDCl 3 ): 2.29 (9 H, s, 38-H, 39-H, 40-H),
2.31 (1 H, m, 2-H ax ), 2.55 (1 H, d, J 11.4, 6-H eq ), 2.78 (1 H, d, J 11.6, 2-H eq ),
3.11 (1 H, m, 6-H ax ), 5.02 (1 H, t, J 5.2, 5-H), 5.38 (1 H, m, 3-H), 5.77 (1 H, t, J
4.4, 4-H), 6.26 (1 H, d, J 16, 9-H), 6.40 (1 H, d, J 16, 18-H), 6.45 (1 H, d, J 16,
27-H), 7.14-7.56 (12 H, m, Ph-H), 7.59 (1 H, d, J 16, 10-H), 7.67 (1 H, d, J 16,
19-H), 7.78 (1 H, d, J 16, 28-H); δ C (125 MHz, CDCl 3 ): 21.06 (C-38), 21.21 (C-
39), 21.29 (C-40), 35.83 (C-2), 35.95 (C-6), 64.72 (C-4), 65.16 (C-3), 71.84 (C-5),
117.28 (C-9), 117.36 (C-18), 117.42 (C-27), 122.30 (C-13, C-15), 122.38 (C-22,
C-24), 122.47 (C-31, C-33), 129.26 (C-12, C-16), 129.58 (C-21, C-25), 129.73
(C-30, C-34), 131.82 (C-11), 132.33 (C-20), 133.57 (C-29), 145.74 (C-10), 145.80
(C-19), 145.98 (C-28), 150.88 (C-14), 151.24 (C-23), 152.55 (C-32), 165.02 (C-
8), 165.56 (C-17), 165.84 (C-20), 168.90 (C-35), 169.19 (C-36), 169.24 (C-37),
171.16 (C-7).
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