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 activity

[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 Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

L-Phenylalanine benzyl ester hydrochloride Usage And Synthesis

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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