(R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride

Base Information

• Chemical Name: (R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride
• CAS No.: 90940-54-8
• Molecular Formula: C12H17 N O2 . Cl H
• Molecular Weight: 243.733
• Hs Code.: 2922499990
• European Community (EC) Number: 823-308-4
• DSSTox Substance ID: DTXSID50513377
• Mol file: 90940-54-8.mol

Synonyms:90940-54-8;(R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride;D-Homophenylalanine ethyl ester hydrochloride;ethyl (2R)-2-amino-4-phenylbutanoate;hydrochloride;D-Homophenylalanine ethyl ester, HCl;MFCD03095466;D-HOMOPHENYLALANINE ETHYL ESTER HYDROC&;ETHYL D-HOMOPHENYLALANINATE HCL;D-HomophenylalanineEthylEsterHydrochloride;SCHEMBL1276908;DTXSID50513377;D-Homophenylalanine Ethyl Ester HCl;AKOS015890009;CS-W014132;HY-W013416;(R)-ethyl 2-amino-4-phenylbutanoate HCl;DS-14739;AM20041383;EN300-1719368;ethyl (2R)-2-amino-4-phenylbutanoate hydrochloride;(R)-2-Amino-4-phenyl-butyric acid ethyl ester hydrochloride;D-Homophenylalanine ethyl ester hydrochloride, >=98.0% (HPLC);Ethyl (2R)-2-amino-4-phenylbutanoate--hydrogen chloride (1/1)

Chemical Property of (R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride

Chemical Property:

• PSA: 52.32000
• LogP: 3.01190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 243.1026065
• Heavy Atom Count: 16
• Complexity: 188

Purity/Quality:

98% ^*data from raw suppliers

D-Homophenylalanine ethyl ester hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)N.Cl
• Isomeric SMILES: CCOC(=O)[C@@H](CCC1=CC=CC=C1)N.Cl
• Uses: D-Homophenylalanine Ethyl Ester Hydrochloride is a useful research chemical. D-Homophenylalanine ethyl ester hydrochloride may be used to synthesize (R)-2-amino-4-phenylbutan-1-ol, an intermediate for 2,6-bis[(4R)-4,5-dihydro-4-(2-phenylethyl)-2-oxazolyl]pyridine ligand.

Technology Process of (R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride

There total 8 articles about (R)-Ethyl 2-amino-4-phenylbutanoate hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

ethyl (R)-2-azido-4-phenylbutanoate (371255-35-5) → (αR)-α-amino-benzenebutanoic acid ethyl ester hydrochloride (90940-54-8)

Guidance literature:

With ammonium chloride; zinc; In ethanol; water; for 0.166667h; Heating;

DOI:10.1016/S0957-4166(01)00285-3

Reference yield:

(-)-ethyl (R)-2-N-benzylamino-4-phenylbutyrate hydrochloride → (αR)-α-amino-benzenebutanoic acid ethyl ester hydrochloride (90940-54-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 25 ℃; under 825.066 Torr;

DOI:10.1055/s-2003-40885

Reference yield:

(S)-2-hydroxy-4-oxo-4-phenylbutanoic acid (146912-63-2) → (αR)-α-amino-benzenebutanoic acid ethyl ester hydrochloride (90940-54-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / H₂; AcOH / Pd/C / 20 °C / 760 Torr

2: 95 percent / H₂SO₄ / 2 h / Heating

3: 100 percent / pyridine / CH₂Cl₂ / 20 °C

4: 87 percent / NaN₃ / dimethylformamide / 6 h / 25 °C

5: 87 percent / Zn; NH₄Cl / ethanol; H₂O / 0.17 h / Heating

With pyridine; sodium azide; sulfuric acid; hydrogen; ammonium chloride; acetic acid; zinc; palladium on activated charcoal; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(01)00285-3

upstream raw materials:

ethyl (R)-2-azido-4-phenylbutanoate

(S)-2-hydroxy-4-phenylbutanoic acid

(S)-ethyl 2-hydroxy-4-phenylbutyrate

(S)-2-hydroxy-4-oxo-4-phenylbutanoic acid

Downstream raw materials:

N-(methyloxalyl)-D-phenylalanine methyl ester

(-)-2-(R)-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}-6-phenylbutyric acid ethyl ester

(-)-2-(R)-(2-aminobenzoylamino)-4-phenylbutyric acid ethyl ester

(βR)-β-amino-benzenebutanol

Refernces

• 1、 Lin, Wen-Qing,He, Ze,Jing, Yi,Cui, Xin,Liu, Hui,Mi, Ai-Qiao. "A practical synthesis of ethyl (R)- and (S)-2-hydroxy-4-phenylbutanoate and D-homophenylalanine ethyl ester hydrochloride from L-malic acid". . p. 1583 - 1587. Retrieved 2007/10/03.