H-D-TRP-OET HCL synthesis
- Product Name:H-D-TRP-OET HCL
- CAS Number:7479-05-2
- Molecular formula:C13H16N2O2
- Molecular Weight:232.28
Yield:7479-05-2 98%
Reaction Conditions:
with thionyl chloride for 12 h;Reflux;
Steps:
Synthesis of ethyl 2-amino-3-(1H-indol-3-yl)propanoate (13)
To a solution of L-tryptophan (5.00 g, 24.50 mmol ) in ethanol (150 mL) was added dropwise thionyl chloride in an ice bath, and the mixture was heated at reflux for 12 h. The solvent was distilled off and the residue was dissolved in water (250 mL), then the mixture was adjust to pH = 10 with an aq solution of NaHCO3. The aqueous was extracted by ethyl acetate (150 mL× 3), and the combined organic phase was washed with brine and dried over anhydrous Na2SO4, then the mixture was concentrated in vacuo to give 13 as a brown oil (5.72 g, 98 %): 1H NMR (400 MHz, CDCl3) δ 8.10 (s, 1H, NH), 7.62 (d, 3JHH = 7.6 Hz, 1H, Ar-H ), 7.37 (d, 3JHH = 8.0 Hz, 1H, Ar-H), 7.20 (t, 3JHH = 7.2 Hz, 1H, Ar-H), 7.13 (t, 3JHH = 7.2 Hz, 1H, Ar-H), 7.08 (s, 1H, Ar-H), 4.14-4.19 (m, 2H, OCH2), 3.82 (dd, 3JHH = 7.6 Hz, 3JHH = 5.2 Hz, 1H, CH), 3.29 (dd, 2JHH = 14.4 Hz, 3JHH = 5.2 Hz, 1H, CH2), 3.05 (dd, 2JHH = 14.4 Hz, 3JHH = 8.0 Hz, 1H, CH2), 1.24 (t, 3JHH = 7.2 Hz, 3H, OCH2CH3).
References:
Song, Hong-Jian;Liu, Yong-Xian;Liu, Yu-Xiu;Huang, Yuan-Qiong;Li, Yong-Qiang;Wang, Qing-Min [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 22,p. 5228 - 5233] Location in patent:supporting information
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