D-Tryptophan methyl ester hydrochloride

CAS NO.：14907-27-8
Empirical Formula: C12H15ClN2O2
Molecular Weight: 254.71
MDL number: MFCD00038992
EINECS: 639-469-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-25 16:21:11

What is D-Tryptophan methyl ester hydrochloride?

Chemical properties

Off-White Crystalline Solid

The Uses of D-Tryptophan methyl ester hydrochloride

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

The Uses of D-Tryptophan methyl ester hydrochloride

Intermediate for the synthesis of Tryptophan derivatives.

What are the applications of Application

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

What are the applications of 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.

Properties of D-Tryptophan methyl ester hydrochloride

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
CAS DataBase Reference	14907-27-8(CAS DataBase Reference)

Safety information for D-Tryptophan methyl ester hydrochloride

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water.