Ethyl L-phenylalaninate hydrochloride Chemical Properties

Melting point:

155-156 °C(lit.)

alpha 

33.7 º (c=2, C2H5OH 21 ºC)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Methanol, Water

form 

Fine Needle-Like Crystalline Solid

color 

White

optical activity

[α]20/D 7.8°, c = 2 in H2O

Water Solubility 

Soluble in methanol and water.

Sensitive 

Hygroscopic

BRN 

3657823

InChI

InChI=1/C11H15NO2.ClH/c1-2-14-11(13)10(12)8-9-6-4-3-5-7-9;/h3-7,10H,2,8,12H2,1H3;1H/t10-;/s3

InChIKey

FPFQPLFYTKMCHN-MEQOOBBNNA-N

SMILES

C1(C=CC=CC=1)C[C@H](N)C(=O)OCC.Cl |&1:7,r|

CAS DataBase Reference

3182-93-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

HS Code 

29224995

MSDS

• Language:English Provider:L-Phenylalanine ethyl ester hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl L-phenylalaninate hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Phenylalanine Ethyl Ester Hydrochloride is an derivative of L-Phenylalanine (P319415), an essential amino acid.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

1. L-phenylalanine (5 g, 30 mmol) was dissolved in anhydrous ethanol (30 mL). 2. slowly add trimethylchlorosilane (TMSCl, 6.915 mL, 54 mmol) to the reaction system at room temperature. 3. A reflux condenser was assembled and the reaction system was heated in an oil bath at 80 °C. 4. 4. The reaction mixture was allowed to react overnight under stirring conditions. 5. On the following day, the reaction system was cooled to room temperature and the reaction solution was subsequently concentrated under reduced pressure. 6. 6. The concentrated residue was dissolved in ether (Et2O). 7. The resulting slurry was filtered and the separated solid product was further washed with ether. 8. The washed solid was dried under high vacuum to afford the target product (S)-ethyl 2-amino-3-phenylpropionate hydrochloride (6.86 g, 99% yield). 9. The structure of the product was confirmed by 1H NPD analysis. 9. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ8.52 (s, 3H), 7.30 (m, 5H), 4.24 (ABX, JAX=7.8 Hz, JBX=6.2 Hz, 1H), 4.11 (m, 2H), 3.17, 3.05 (ABX, JAB=-14 Hz, JBX=5.8 Hz, JAX=7.6 Hz, 2H), 1.09 (t, J=6.8 Hz, 3H).

References

[1] Patent: US2017/71964, 2017, A1. Location in patent: Paragraph 0594-0595
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944
[3] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6900 - 6903
[4] Chemical Communications, 2011, vol. 47, # 42, p. 11784 - 11786
[5] Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 7/8, p. 413 - 418

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