D-Tryptophan methyl ester hydrochloride Chemical Properties

Melting point:

213-216 °C(lit.)

Density 

1.337g/cm3 at 20℃

refractive index 

-19 ° (C=5, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

White to Off-White

optical activity

[α]20/D 18°, c = 5 in methanol

Water Solubility 

Soluble in water (150 mg/ml), dimethyl sulfoxide and methanol (50 mg/ml).

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|

LogP

1.089

CAS DataBase Reference

14907-27-8(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

D-Tryptophan methyl ester hydrochloride Usage And Synthesis

Description

D-Tryptophan Methyl Ester Hydrochloride is an intermediate in the synthesis of Tryptophan derivatives. Soluble in water (150 mg/ml), dimethyl sulfoxide and methanol (50 mg/ml). Incompatible with strong oxidizing agents. Store under room temperature.

Chemical Properties

Off-White Crystalline Solid

Uses

Intermediate for the synthesis of Tryptophan derivatives.

Uses

D-Tryptophan Methyl Ester Hydrochloride is an intermediate in the synthesis of Tryptophan derivatives.

Application

The Pictet–Spengler reaction of D-Tryptophan methyl ester hydrochloride with piperonal in various solvents has been extensively studied, the solvent-dependence of stereoselectivities could be principally attributed to the solubility difference between cis and trans products 5-HCl in the used solvent, the best stereoselectivity (cis/trans = 99:1) was obtained using nitromethane or acetonitrile as the solvent. Cialis, 12a-epi-Cialis, deuterium-labeled, 3,3,12a-d3-Cialis, and 3,3,12a-d3-12a-epi-Cialis could be efficiently synthesized from D-Tryptophan methyl ester hydrochloride[1].

Synthesis

D-tryptophan and methyl sulfonate are reacted in a solvent at 25 to 100°C to generate D-tryptophan methyl ester sulfonate. Dissolve the obtained D-tryptophan methyl ester sulfonate in water and adjust the pH to alkaline with alkali to convert it into D-tryptophan methyl ester. After the reaction, extract with an organic solvent, add a desiccant for dehydration, and obtain an extract containing D-tryptophan methyl ester. Finally, dry hydrogen chloride gas is passed into the obtained extract containing D-tryptophan methyl ester for reaction to obtain D-tryptophan methyl ester hydrochloride.

References

[1] Xiao-Xin Shi. “Highly stereoselective Pictet–Spengler reaction of d-tryptophan methyl ester with piperonal: convenient syntheses of Cialis (Tadalafil), 12a-epi-Cialis, and their deuterated analogues.” Tetrahedron, asymmetry 19 4 (2008): Pages 435-442.

D-Tryptophan methyl ester hydrochloride(14907-27-8)Related Product Information

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