D-Tryptophan methyl ester hydrochloride

Bezeichnung:D-Tryptophan methyl ester hydrochloride

CAS-Nr14907-27-8

Englisch Name:D-Tryptophan methyl ester hydrochloride

CBNumberCB9459476

SummenformelC12H15ClN2O2

Molgewicht254.71

MOL-Datei14907-27-8.mol

D-Tryptophan methyl ester hydrochloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	213-216 °C(lit.)
Dichte	1.337g/cm3 at 20℃
Brechungsindex	-19 ° (C=5, MeOH)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	DMSO, (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand	Solid
Farbe	White to Off-White
Optische Aktivität	[α]20/D 18°, c = 5 in methanol
Wasserlöslichkeit	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 Datenbank	14907-27-8(CAS DataBase Reference)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
HS Code	29339900

Gefahreninformationscode (GHS)

D-Tryptophan methyl ester hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
Off-White Crystalline Solid
Verwenden
Intermediate for the synthesis of Tryptophan derivatives.
Verwenden
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].
Synthese
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.
Einzelnachweise
[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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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