ChemicalBook > CAS DataBase List > D-Tryptophan methyl ester hydrochloride

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
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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)
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Safety

Safety Statements 
24/25
WGK Germany 
3
HS Code 
29339900
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
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
Sigma-Aldrich
Product number
364509
Product name
D-Tryptophan methyl ester hydrochloride
Purity
98%
Packaging
5g
Price
$42.1
Updated
2022/05/15
TCI Chemical
Product number
T2442
Product name
D-Tryptophan Methyl Ester Hydrochloride
Purity
>98.0%(N)
Packaging
5g
Price
$25
Updated
2025/07/31
TCI Chemical
Product number
T2442
Product name
D-Tryptophan Methyl Ester Hydrochloride
Purity
>98.0%(N)
Packaging
25g
Price
$100
Updated
2025/07/31
Usbiological
Product number
237255
Product name
D-Tryptophan methyl ester hydrochloride 99+%
Packaging
5g
Price
$177
Updated
2021/12/16
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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].

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

Preparation Products

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View Lastest Price from D-Tryptophan methyl ester hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
D-Tryptophan methyl ester hydrochloride 14907-27-8
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kgs
Release date
2021-08-27
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
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
Sichuan HongRi Pharma-Tech Co.,Ltd
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

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