ChemicalBook CAS DataBase List H-D-TRP-OET HCL

H-D-TRP-OET HCL synthesis

6synthesis methods

Product Name:H-D-TRP-OET HCL
CAS Number:7479-05-2
Molecular formula:C13H16N2O2
Molecular Weight:232.28

64-17-5 Synthesis

64-17-5
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73-22-3 Synthesis

73-22-3
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7479-05-2
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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, ³J_HH = 7.6 Hz, 1H, Ar-H ), 7.37 (d, ³J_HH = 8.0 Hz, 1H, Ar-H), 7.20 (t, ³J_HH = 7.2 Hz, 1H, Ar-H), 7.13 (t, ³J_HH = 7.2 Hz, 1H, Ar-H), 7.08 (s, 1H, Ar-H), 4.14-4.19 (m, 2H, OCH₂), 3.82 (dd, ³J_HH = 7.6 Hz, ³J_HH = 5.2 Hz, 1H, CH), 3.29 (dd, ²J_HH = 14.4 Hz, ³J_HH = 5.2 Hz, 1H, CH₂), 3.05 (dd, ²J_HH = 14.4 Hz, ³J_HH = 8.0 Hz, 1H, CH₂), 1.24 (t, ³J_HH = 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

1H-Indole, 3-[[(2S,5R)-3,6-diethoxy-2,5-dihydro-5-(1-methylethyl)-2-pyrazinyl]methyl]-2-(trimethylsilyl)-

220906-02-5
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7479-05-2
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References

L-Tryptophan, N-[(phenylmethoxy)carbonyl]-, ethyl ester

41844-69-3
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7479-05-2
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615-43-0
414 suppliers
$5.00/5g

7479-05-2
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Pyrazine, 3,6-diethoxy-2,5-dihydro-2-(1-methylethyl)-5-[3-(trimethylsilyl)-2-propyn-1-yl]-, (2R,5S)-

220906-01-4
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7479-05-2
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References