| Identification | More | [Name]
L-Phenylalanine benzyl ester hydrochloride | [CAS]
2462-32-0 | [Synonyms]
H-PHE-OBZL HCL
L-PHENYLALANINE BENZYL ESTER HYDROCHLORIDE
L-PHENYLALANINE BENZYL ESTER HYDROCHLORIDE SALT
PHENYLALANINE-OBZL HCL
PHE-OBZL HCL
benzyl 3-phenyl-L-alaninate hydrochloride
L-Phenylalanine Benzyl Ester HCl
Phenylalanine, benzyl ester hydrochloride
H-PHE-OBZL.HCI
H-L-Phe-OBzl*HCl | [EINECS(EC#)]
219-558-3 | [Molecular Formula]
C16H18ClNO2 | [MDL Number]
MFCD00043249 | [Molecular Weight]
291.77 | [MOL File]
2462-32-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
197-200 °C | [alpha ]
-13 º (c=1% in 80% acetic acid) | [refractive index ]
-12 ° (C=1, 80% acetic acid) | [storage temp. ]
Store at RT. | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [Water Solubility ]
Soluble in water | [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 | [InChI]
InChI=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 | [InChIKey]
CEXFHIYDTRNBJD-AVAJOTNLNA-N | [SMILES]
C1(=CC=CC=C1)C[C@H](N)C(=O)OCC1C=CC=CC=1.Cl |&1:7,r| | [CAS DataBase Reference]
2462-32-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29224999 |
| Hazard Information | Back Directory | [Chemical Properties]
White crystal | [Uses]
L-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 suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
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 |
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