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L-Phenylalanine benzyl ester hydrochloride

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CAS:2462-32-0
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  • H-L-Phe-OBzl.HCl
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  • 2026-03-20
  • CAS:2462-32-0
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  • Purity: 98%
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L-Phenylalanine benzyl ester hydrochloride Basic information
Product Name:L-Phenylalanine benzyl ester hydrochloride
Synonyms:benzyl 3-phenyl-L-alaninate hydrochloride;L-Phenylalanine Benzyl Ester HCl;H-PHE-OBZL·HCL;L-Phenylalanine benzyl ester hydrochloride≥ 99% (HPLC);H-PHE-OBZL HCL;PHE-OBZL HCL;PHENYLALANINE-OBZL HCL;L-PHENYLALANINE BENZYL ESTER HYDROCHLORIDE
CAS:2462-32-0
MF:C16H18ClNO2
MW:291.77
EINECS:219-558-3
Product Categories:Phenylalanine [Phe, F];Amino Acids and Derivatives;Amino Acid Benzyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Peptide Synthesis;Phenylalanine;Amino Acid Derivatives;Amino Acids
Mol File:2462-32-0.mol
L-Phenylalanine benzyl ester hydrochloride Structure
L-Phenylalanine benzyl ester hydrochloride Chemical Properties
Melting point 197-200 °C
alpha -13 º (c=1% in 80% acetic acid)
refractive index -12 ° (C=1, 80% acetic acid)
storage temp. Inert atmosphere,Room Temperature
Water Solubility Soluble in water
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form Crystalline Powder
color White to off-white
Optical Rotation[α]20/D 13±1°, c = 1% in acetic acid: water (4:1)
BRN 3919200
Major Applicationpeptide synthesis
InChIInChI=1/C16H17NO2.ClH/c17-15(11-13-7-3-1-4-8-13)16(18)19-12-14-9-5-2-6-10-14;/h1-10,15H,11-12,17H2;1H/t15-;/s3
InChIKeyCEXFHIYDTRNBJD-AVAJOTNLNA-N
SMILESC1(=CC=CC=C1)C[C@H](N)C(=O)OCC1C=CC=CC=1.Cl |&1:7,r|
CAS DataBase Reference2462-32-0(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 29224999
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
L-Phenylalanine benzyl ester hydrochloride Usage And Synthesis
Chemical PropertiesWhite crystal
UsesL-Phenylalanine Benzyl Ester Hydrochloride is a commonly used reactant for the synthesis of L-isoserine derivatives as aminopeptidase N inhibitors and PF-04449913 as a potent and orally bioavailable inhibitor of smoothened.
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesis
BOC-PHE-OBZL

66617-58-1

L-Phenylalanine benzyl ester hydrochloride

2462-32-0

The general procedure for the synthesis of L-phenylalanine benzyl ester hydrochloride from (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropionate was as follows: benzyl (2S)-2-(tert-butoxycarbonylamino)-3-phenylpropionate (12.8 g, 36 mmol) was dissolved in an ether solution of 2 M HCl (90 mL) and a dioxane solution of 4 M HCl (18 mL). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was diluted with hexane (100 mL) and subsequently filtered to afford L-phenylalanine benzyl ester hydrochloride (7.98 g, 76% yield) as a white fine powder. The product was characterized by 1H NMR (CD3OD, 400 MHz): δ (ppm) 7.40-7.15 (m, 10H), 5.23 (s, 2H), 4.36-4.31 (m, 1H), 3.26-3.12 (m, 2H).

References[1] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4235 - 4243
[2] Patent: US9441012, 2016, B2. Location in patent: Page/Page column 67
[3] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 14, p. 1497 - 1499
[4] Journal of Enzyme Inhibition and Medicinal Chemistry, 2012, vol. 27, # 2, p. 302 - 310
[5] Chemistry - A European Journal, 2012, vol. 18, # 21, p. 6528 - 6541
L-Phenylalanine benzyl ester hydrochloride Preparation Products And Raw materials
Raw materialsBOC-PHE-OBZL-->Diethyl ether-->Hydrochloric acid-->1,4-Dioxane
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