D-Tryptophan methyl ester hydrochloride
- Product Name
- D-Tryptophan methyl ester hydrochloride
- CAS No.
- 14907-27-8
- Chemical Name
- D-Tryptophan methyl ester hydrochloride
- Synonyms
- D-TRYPTOPHAN METHYL ESTER HCL;Methyl D-Tryptophanate Hydrochloride;Trp-OMe;D-TRYPTOPHAN METHYL ESTER;ANAM-002;D-TRP.OME.HCL;D-Trp-OCH3.Hcl;H-D-TRP-OME·HCL;H-D-TRP-OME HCL;D-Tryptophan methyl
- CBNumber
- CB9459476
- Molecular Formula
- C12H15ClN2O2
- Formula Weight
- 254.71
- MOL File
- 14907-27-8.mol
D-Tryptophan methyl ester hydrochloride Property
- 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
- 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
- Safety Statements
- 24/25
- WGK Germany
- 3
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
N-Bromosuccinimide Price
- Product number
- PH017490
- Product name
- Methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate
- Purity
- AldrichCPR
- Packaging
- 1g
- Price
- $81.6
- Updated
- 2023/06/20
- Product number
- 364509
- Product name
- D-Tryptophan methyl ester hydrochloride
- Purity
- 98%
- Packaging
- 5g
- Price
- $42.1
- Updated
- 2022/05/15
- Product number
- T2442
- Product name
- D-Tryptophan Methyl Ester Hydrochloride
- Purity
- >98.0%(N)
- Packaging
- 5g
- Price
- $25
- Updated
- 2024/03/01
- Product number
- T2442
- Product name
- D-Tryptophan Methyl Ester Hydrochloride
- Purity
- >98.0%(N)
- Packaging
- 25g
- Price
- $100
- Updated
- 2024/03/01
- Product number
- H60622
- Product name
- D-Tryptophan methyl ester hydrochloride, 98%
- Packaging
- 5g
- Price
- $79.5
- Updated
- 2024/03/01
D-Tryptophan methyl ester hydrochloride Chemical Properties,Usage,Production
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].
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
Preparation Products
D-Tryptophan methyl ester hydrochloride Suppliers
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- Country
- Europe
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View Lastest Price from D-Tryptophan methyl ester hydrochloride manufacturers
- Product
- D-Tryptophan methyl ester HCL 14907-27-8
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98+
- Supply Ability
- 1T
- Release date
- 2024-04-08
- Product
- D-Tryptophan methyl ester hydrochloride 14907-27-8
- Price
- US $100.00-75.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000
- Release date
- 2024-08-22
- Product
- D-Tryptophan methyl ester hydrochloride 14907-27-8
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 98
- Supply Ability
- 1000
- Release date
- 2024-09-24