| Identification | More | [Name]
Methyl L-tryptophanate hydrochloride | [CAS]
7524-52-9 | [Synonyms]
H-TRP-OME HCL
L-2-AMINO-3-INDOLYLPROPANOIC ACID METHYL ESTER HYDROCHLORIDE
L-A-AMINO-3-INDOLEPROPIONIC ACID METHYL ESTER HYDROCHLORIDE
L-B-3-INDOLYLALANINE METHYL ESTER HYDROCHLORIDE
L-TRYPTOPHAN METHYL ESTER HCL
L-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE
L-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE SALT
methyl (2r)-2-amino-3-(1h-indol-3-yl)propanoate hydrochloride
METHYL L-TRYPTOPHANATE HYDROCHLORIDE
(S)-2-AMINO-3-(1H-INDOL-3-YL)-PROPIONIC ACIDMETHYL ESTER HYDROCHLORIDE
TRYPTOPHAN-OME HCL
H-Trp-OMe•
methyl L-tryptophanate monohydrochloride
METHYL TRYPTOPHANATE HCL
L-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE 98+%
Trp-Ome.HCl
L-Tryptophan, methyl ester, monohydrochloride
H-L-Trp-OMe*HCl
L-Tryptophane methyl ester hydrochloride
(S)-Tryptophan Methyl Ester Monohydrochloride | [EINECS(EC#)]
231-385-5 | [Molecular Formula]
C12H15ClN2O2 | [MDL Number]
MFCD00066134 | [Molecular Weight]
254.71 | [MOL File]
7524-52-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white powder | [Melting point ]
218-220 °C(lit.) | [alpha ]
18 º (c=5 CH3OH) | [refractive index ]
19.5 ° (C=5, MeOH) | [storage temp. ]
-15°C | [solubility ]
DMSO (Slightly), Methanol (Sparingly) | [form ]
Powder | [color ]
White to off-white | [Optical Rotation]
[α]20/D +18°, c = 5 in methanol | [Usage]
Amino acid derivative that may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550) | [BRN ]
4240280 | [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| | [CAS DataBase Reference]
7524-52-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Methyl L-tryptophanate hydrochloride is White to off-white powder
| [Uses]
L-Tryptophan methyl ester hydrochloride can be used as a reactant to prepare:
- Oxamoyl derivatives of N-(2-aminobenzoyl)-L-tryptophan (dipeptides) by acylation reaction with 3,1-benzoxazinones.
- Tadalafil (Cialis), a type-V phosphodiesterase (PDE5) inhibitor.
- Isoroquefortine C.
| [Uses]
Amino acid derivative that may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550). | [Uses]
Methyl L-tryptophanate hydrochloride may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550)
| [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
(2) Preparation of L-tryptophan methyl ester hydrochloride: 60 mL of methanol was added to a 100 mL round-bottomed flask under ice bath conditions. Subsequently, 4 mL of sulfoxide chloride (SOCl2) was slowly added dropwise through a constant-pressure dropping funnel (equipped with a drying tube at the top), and NaOH solution was used to absorb the resulting exhaust gas. After the reaction mixture was reacted under stirring conditions for 1 h, 8 mmol of L-tryptophan (3d) was added and stirring was continued for 30 min at room temperature. After that, the reaction system was warmed up to 66 °C and the reaction was refluxed for 6 hours. The reaction process was monitored by thin-layer chromatography (TLC) using 2% ninhydrin ethanol solution as a color developer until the raw material spot disappeared. Upon completion of the reaction, the solvent was removed by evaporation to give L-tryptophan methyl ester hydrochloride in 100% yield. | [References]
[1] Tetrahedron, 2001, vol. 57, # 51, p. 10181 - 10189
[2] Patent: US2014/206741, 2014, A1. Location in patent: Paragraph 0111
[3] European Journal of Medicinal Chemistry, 2016, vol. 114, p. 318 - 327
[4] New Journal of Chemistry, 2018, vol. 42, # 16, p. 13549 - 13557
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 41, p. 8280 - 8287 |
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