Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
(1R, 3R, 4S, 5R)-1-dimethoxycinnamoylquinic acid, (60)-p97
To a solution of quinic acid lactone 53 (0.200 g, 0.50 mmol) was dissolved in THF (8
ml) and treated with LiOH (0.012 g, 0.50 mmol in 4ml H 2 O) at room temperature.
The solution was stirred for 3 days at room temperature, acidified by using 2M HCl
(10 ml) solution and extracted with dichloromethane (50 ml). The organic layer was
dried with MgSO 4 and filtered. The solvent was removed under reduced pressure to
give the title compound 60 as a pale yellow powder (0.158 g, 84%). Rf 0.38
[chloroform: acetone (10:1)]; mp 150 ºC; ν max (Nujol)/cm -1 : 3368 (OH), 2954
(COOH), 2854 (C-H), 1797, 1712 (C=O), 1628 (C Ar =C Ar ), 1156, 1075 (C-O); δ H (500
MHz, D 2 O): 1.97 (1 H, dd, J 13.7 and 10.9, 6-H ax ), 2.29 (1 H, dd, J 15.5 and 3.4, 2-
H ax ), 2.50 (1 H, ddd, J 13.7, 4.4 and 3.4, 6-H eq ), 2.59 (1 H, dt, J 12.8 and 3.4, 2-H eq ),
3.63 (1 H, dd, J 9.2 and 3.4, 4-H), 3.86 (3 H, s, 17-H), 3.88 (3 H, s, 18-H), 4.16 (1 H,
ddd, J 10.9, 9.2 and 4.4, 5-H), 4.27 (1 H, q, J 3.4, 3-H), 6.43 (1 H, d, J 15.9, 9-H),
6.49 (1 H, d, J 8.3, 12-H), 7.18 (1 H, d, J 1.9, 15-H), 7.20 (1 H, dd, J 8.3 and 1.9, 16-
H), 7.63 (1 H, d, J 15.9, 10-H); δ C (125 MHz, D 2 O): 34.3 (C-6), 38.51 (C-2), 55.64
(C-17), 55.75 (C-18), 66.13 (C-5), 68.12 (C-3), 74.46 (C-4), 80.93 (C-1), 110.26 (C-
12), 111.57 (C-15), 114.77 (C-9), 123.65 (C-16), 127.19 (C-11), 146.93 (C-10),
148.26 (C-13), 150.69 (C-14), 168.16 (C-8), 175.53 (C-7); MS, m/z (CI): 382 [M + ],
365 [M-OH]; CHN: (C 18 H 22 O 9 382 g/mol requires: C, 56.5%; H; 5.75%), Found: C,
47.71%; H, 5.37%.
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