(R)-Ethyl 3-amino-3-phenylpropanoate

Base Information

• Chemical Name: (R)-Ethyl 3-amino-3-phenylpropanoate
• CAS No.: 3082-68-6
• Molecular Formula: C11H15 N O2
• Molecular Weight: 193.246
• Hs Code.: 2922499990
• European Community (EC) Number: 608-545-1
• DSSTox Substance ID: DTXSID40358774
• Nikkaji Number: J1.302.445F
• Wikidata: Q82139612
• Mol file: 3082-68-6.mol

Synonyms:3082-68-6;(R)-Ethyl 3-amino-3-phenylpropanoate;ethyl (3R)-3-amino-3-phenylpropanoate;(R)-BETA-PHENYLALANINE ETHYL ESTER;(betaR)-beta-Aminobenzenepropanoic Acid Ethyl Ester;ethyl (R)-3-amino-3-phenylpropanoate;(R)-3-Amino-3-phenylpropionicacidethylester;Benzenepropanoic acid, beta-amino-, ethyl ester, (betaR)-;(R)-Ethyl3-amino-3-phenylpropanoate;beta-phenylalanine Ethyl Ester;SCHEMBL1138682;DTXSID40358774;MFCD06761764;racemic beta-phenylalanine ethyl ester;AKOS010393668;(R)-3-Phenyl-beta-alanine ethyl ester;EN300-148322;J-018157;(R)-3-AMINO-3-PHENYLPROPANOIC ACID ETHYL ESTER

Chemical Property of (R)-Ethyl 3-amino-3-phenylpropanoate

Chemical Property:

• Boiling Point: 299.0±28.0 °C(Predicted)
• PKA: 7.75±0.10(Predicted)
• PSA: 52.32000
• Density: 1.075±0.06 g/cm3(Predicted)
• LogP: 2.33990
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 176

Purity/Quality:

97% ^*data from raw suppliers

(βR)-β-AminobenzenepropanoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(C1=CC=CC=C1)N
• Isomeric SMILES: CCOC(=O)C[C@H](C1=CC=CC=C1)N
• Uses: (βR)-β-Aminobenzenepropanoic Acid Ethyl Ester is used in the three-step synthesis of β-amino acids. Also used in the microbial production of β-phenylalanine ethyl esters.

Technology Process of (R)-Ethyl 3-amino-3-phenylpropanoate

There total 23 articles about (R)-Ethyl 3-amino-3-phenylpropanoate 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: 93.0%

ethyl 3-amino-3-phenylprop-2-enoate (33831-72-0) → (R)-3-amino-3-phenylpropionic acid ethyl ester (3082-68-6)

Guidance literature:

With trichlorosilane; C₁₉H₃₂N₂O₂S; water; In toluene; at -40 ℃; for 36h; Solvent; Reagent/catalyst; Temperature; enantioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201501061

Reference yield: 86.0%

ethyl 3-(benzylamino)-3-phenylpropanoate (1282538-74-2) → (R)-3-amino-3-phenylpropionic acid ethyl ester (3082-68-6)

Guidance literature:

With 10% Pd(OH)2/C; hydrogen; In ethanol; at 20 ℃; for 8h; under 760.051 Torr; optical yield given as %ee;

DOI:10.1002/chem.201003105

Reference yield: 85.0%

(R)-3-amino-3-phenylpropionic acid ethyl ester hydrochloride (340188-50-3) → (R)-3-amino-3-phenylpropionic acid ethyl ester (3082-68-6)

Guidance literature:

With sodium carbonate; In diethyl ether; water;

upstream raw materials:

3-amino-3-phenylpropionic acid ethyl ester

ethanol

1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene

(1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide

Downstream raw materials:

(S)-3-hydroxy-3-phenylpropanoic acid

Cinnamic acid

(R)-3-amino-3-phenyl-1-propanol

(R)-3-phenyl-3-aminopropionic acid

Refernces

• 1、 Mokhallalati,Pridgen. "Lead tetraacetate cleavage of chiral phenylglycinol derived secondary amines without racemization". . p. 2055 - 2064. Retrieved 1993.
• 2、 BuΒ, Oliver,Voss, Moritz,Delavault, André,Gorenflo, Pascal,Syldatk, Christoph,Bornscheuer, Uwe,Rudat, Jens. "Β-phenylalanine ester synthesis from stable β-keto ester substrate using engineered ω-transaminases". . . Retrieved 2018/05/30.
• 3、 -. "BICYCLIC-PYRIMIDINEDIONE COMPOUNDS". Paragraph 0146; 0147. . Retrieved 2016/07/27.