D,L-Tryptophan Methyl Ester Hydrochloride Chemical Properties

Melting point:

221-222

storage temp. 

Inert atmosphere,2-8°C

solubility 

Methanol, Water

form 

Solid

color 

Off-white to white

InChI

InChI=1S/C12H14N2O2.ClH/c1-16-12(15)10(13)6-8-7-14-11-5-3-2-4-9(8)11;/h2-5,7,10,14H,6,13H2,1H3;1H

InChIKey

XNFNGGQRDXFYMM-UHFFFAOYSA-N

SMILES

C12C=CC=CC=1NC=C2CC(N)C(=O)OC.Cl

CAS DataBase Reference

5619-09-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Hazard Note 

Irritant

HS Code 

2933998090

D,L-Tryptophan Methyl Ester Hydrochloride Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Amino acid derivative that may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550).

Uses

Amino acid derivative， D,L-Tryptophan Methyl Ester Hydrochloride may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550)

Synthesis

The general procedure for the synthesis of L-tryptophan methyl ester hydrochloride from methanol and L-tryptophan was as follows: L-tryptophan (18.2 mmol) was dissolved in methanol (20 mL) at 0 °C with stirring. Thionyl chloride (1.6 mL, 22 mmol) was added slowly and dropwise over 10 min. Subsequently, the reaction mixture was gradually warmed to room temperature and heated under reflux conditions for 3 hours. Upon completion of the reaction, the solvent and volatiles were removed by distillation under reduced pressure. The resulting product was ground with ethyl acetate to give L-tryptophan methyl ester hydrochloride as a colorless solid in 100% yield. The product was a white solid with a yield of 4.63 g. Its 1H NMR (400 MHz, CD3OD) and 13C NMR (100 MHz, CD3OD) data were consistent with those reported in the literature, confirming the structure and purity of the product.

References

[1] Tetrahedron, 2001, vol. 57, # 51, p. 10181 - 10189
[2] Patent: US2014/206741, 2014, A1. Location in patent: Paragraph 0111
[3] European Journal of Medicinal Chemistry, 2016, vol. 114, p. 318 - 327
[4] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13549 - 13557
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 41, p. 8280 - 8287

D,L-Tryptophan Methyl Ester Hydrochloride(5619-09-0)Related Product Information

• D,L-Tryptophan Methyl Ester Hydrochloride
• D-Tryptophan methyl ester hydrochloride
• Methyl L-tryptophanate hydrochloride
• Ethyl L-tryptophanate hydrochloride
• Benzyl L-tryptophanate hydrochloride
• TRYPTAMINE HYDROCHLORIDE
• L-Tryptophan
• DL-Tryptophan
• DL-TRYPTOPHAN-N-OCTYL ESTER HYDROCHLORIDE
• H-D-TRP-OET HCL
• H-TRP-OTBU HCL
• DL-TRYPTOPHAN ETHYL ESTER HYDROCHLORIDE
• L-5-HYDROXYTRYPTOPHAN METHYL ESTER HYDROCHLORIDE
• 5-HYDROXY-DL-TRYPTOPHAN ETHYL ESTER HYDROCHLORIDE
• L-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID ETHYL ESTER HYDROCHLORIDE
• Z-L-TRYPTOPHAN 2,4,5-TRICHLOROPHENYL ESTER
• DL-2-AMINO-3-INDOLYLPROPANOIC ACID BUTYL ESTER HYDROCHLORIDE
• H-LEU-TRP-OME HCL