7-BENZYLOXY-D,L-TRYPTOPHAN synthesis
- Product Name:7-BENZYLOXY-D,L-TRYPTOPHAN
- CAS Number:66866-40-8
- Molecular formula:C18H18N2O3
- Molecular Weight:310.35
87-32-1
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66866-40-8
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Yield:66866-40-8 5%
Reaction Conditions:
with sodium hydroxide for 17 h;Heating / reflux;
Steps:
8.32 Preparation of (+/-)-7-benzyloxytryptophan
A suspension of the intermediate N-acetyltryptophan in 3 N sodium hydroxide was heated at reflux for 17 hours, then cooled to room temperature.The mixture was diluted with water (50 ML), washed with diethyl ether (50 ML), slurried with charcoal (1 g), and filtered through a plug of silica gel (20 g), eluding with water (100 ML).The filtrate was acidified to PH 4 with 6 N HCl (1 ML), and the solution was filtered through a plug of DOWEX 50*8-100 ion-exchange resin (100 g), eluding with concentrated ammonium hydroxide/methanol (1:3), to provide Intermediate 32 as a gray powder (0.040 g, 5% over two steps): 1H NMR (300 MHz, CD3OD): δ 7.51 (d, J=7.0 Hz, 2H), 7.39-7.29 (m, 3H), 7.17 (d, J=7.9 Hz, 1H), 7.04 (s, 1H), 6.91 (t, J=7.6 Hz, 1H), 6.68 (d, J=7.7 Hz, 1H), 5.21 (s, 2H), 4.72-4.68 (m, H), 3.34-3.29 (m, 1H), 3.16-3.09 (m, 1H) ppm.
References:
US2003/225092,2003,A1 Location in patent:Page 20
20289-27-4
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66866-40-8
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$40.00/10mg
6326-44-9
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94067-27-3
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66866-40-8
48 suppliers
$40.00/10mg