Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
(1R, 3R, 4S, 5R)-1-cinnamoylquinic acid, (59)-p91
To a solution of quinic acid lactone 52 (0.400 g, 1.160 mmol) was dissolved in THF
(8 ml) and treated with LiOH (0.028 g, 1.16 mmol in 4ml H 2 O) at room temperature.
The solution was stirred for 2 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 59 as a pale yellow powder (0.150 g, 40.1%). Rf 0.40
[chloroform: acetone (10:1)]; mp 164 ºC; ν max (Nujol)/cm -1 : 3407 (OH), 2954
(COOH), 2854 (C-H), 1792, 1694 (C=O), 1636 (C Ar =C Ar ), 1062, 1031 (C-O); δ H (500
MHz, D 2 O): 1.95 (1 H, dd, J 11 and 1.95, 6-H ax ), 2.26 (1 H, dd, J 15 and 3.5, 2-H ax ),
2.53 (1 H, m, 6-H eq ), 2.57 (1 H, m, 2-H eq ), 3.60 (1 H, dd, J 9.5 and 3.5, 4-H), 4.11 (1
H, m, 5-H), 4.25 (1 H, dt, J 15.5 and 3.5, 3-H), 6.61 (1 H, d, J 16, 9-H), 7.67-7.47 (5
H, m, Ph-H), 7.75 (1 H, d, J 16, 10-H); δ C (125 MHz, D 2 O): 34.61 (C-6), 38.73 (C-2),
66.37 (C-5), 68.88 (C-3), 74.71 (C-4), 81.56 (C-1), 117.60 (C-9), 128.62, 128.72,
129.39, 131.14, 131.32 (C-12, C13, C-14, C-15, C-16), 134.19 (C-11), 147.26 (C-10),
168.19 (C-8), 175.95 (C-7); MS, m/z (CI): 322 [M + ], 323 [M+H], 131 [M-C 9 H 7 O];
CHN: (C 16 H 18 O 7 322 g/mol requires: C, 59.62%; H, 5.59%), Found: C, 60.83%; H,
5.65%.
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