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| | D-Tryptophan methyl ester hydrochloride Basic information |
| | 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 Rotation | [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 Statements | 24/25 | | WGK Germany | 3 | | HS Code | 29339900 |
| | 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].
| | reaction suitability | reaction type: solution phase peptide synthesis | | 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.
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| | D-Tryptophan methyl ester hydrochloride Preparation Products And Raw materials |
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