Methyl L-tryptophanate hydrochloride Chemical Properties

Melting point:

218-220 °C(lit.)

alpha 

18 º (c=5 CH3OH)

refractive index 

19.5 ° (C=5, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Sparingly)

form 

Powder

color 

White to off-white

optical activity

[α]20/D +18°, c = 5 in methanol

BRN 

4240280

InChI

InChI=1/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/t10-;/s3

InChIKey

XNFNGGQRDXFYMM-MEQOOBBNNA-N

SMILES

C12C=CC=CC=1NC=C2C[C@H](N)C(=O)OC.Cl |&1:10,r|

CAS DataBase Reference

7524-52-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl L-tryptophanate hydrochloride Usage And Synthesis

Chemical Properties

Methyl L-tryptophanate hydrochloride is White to off-white powder

Uses

Methyl L-tryptophanate hydrochloride may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550)

Uses

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

Uses

L-Tryptophan methyl ester hydrochloride can be used as a reactant to prepare:

• Oxamoyl derivatives of N-(2-aminobenzoyl)-L-tryptophan (dipeptides) by acylation reaction with 3,1-benzoxazinones.
• Tadalafil (Cialis), a type-V phosphodiesterase (PDE5) inhibitor.
• Isoroquefortine C.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

(2) Preparation of L-tryptophan methyl ester hydrochloride: 60 mL of methanol was added to a 100 mL round-bottomed flask under ice bath conditions. Subsequently, 4 mL of sulfoxide chloride (SOCl2) was slowly added dropwise through a constant-pressure dropping funnel (equipped with a drying tube at the top), and NaOH solution was used to absorb the resulting exhaust gas. After the reaction mixture was reacted under stirring conditions for 1 h, 8 mmol of L-tryptophan (3d) was added and stirring was continued for 30 min at room temperature. After that, the reaction system was warmed up to 66 °C and the reaction was refluxed for 6 hours. The reaction process was monitored by thin-layer chromatography (TLC) using 2% ninhydrin ethanol solution as a color developer until the raw material spot disappeared. Upon completion of the reaction, the solvent was removed by evaporation to give L-tryptophan methyl ester hydrochloride in 100% yield.

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

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