Introduction：Basic information about D-Tryptophan methyl ester hydrochloride CAS 14907-27-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
D-Tryptophan methyl ester hydrochloride Basic information
| Product Name: | D-Tryptophan methyl ester hydrochloride |
| Synonyms: | (R)-Tryptophan Methyl Ester Monohydrochloride;Methyl D-Tryptophanate Hydrochloride;H-D-TRP-OME·HCL;D-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE 99%;D-TRP.OME.HCL;(S)-2-Amino-3-(1H-indol-3-yl)-propionic acid methyl ester hydrochloride;Methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride;D-Tryptophane methyl ester hydrochloride |
| CAS: | 14907-27-8 |
| MF: | C12H15ClN2O2 |
| MW: | 254.71 |
| EINECS: | 639-469-7 |
| Product Categories: | Intermediate of Tadalafil;tadalafil intermediate;Tryptophan;Tryptophan [Trp, W];Amino Acids and Derivatives;Amino Acids 13C, 2H, 15N;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acids;Amino Acids Derivatives;Amino Acids & Derivatives;Amino Acid Derivatives;Peptide Synthesis |
| Mol File: | 14907-27-8.mol |
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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 Information
| Safety Statements | 24/25 |
| WGK Germany | 3 |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
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. |
D-Tryptophan methyl ester hydrochloride Preparation Products And Raw materials
| Raw materials | Methanol-->L-Tryptophan-->Ethanol-->Thionyl chloride |
