(S)-Ethyl 3-amino-3-phenylpropanoate

Base Information

• Chemical Name: (S)-Ethyl 3-amino-3-phenylpropanoate
• CAS No.: 3082-69-7
• Molecular Formula: C11H15 N O2
• Molecular Weight: 193.246
• Hs Code.: 2922499990
• European Community (EC) Number: 608-546-7
• DSSTox Substance ID: DTXSID80358773
• Nikkaji Number: J1.302.446D
• Wikidata: Q82139610
• Mol file: 3082-69-7.mol

Synonyms:3082-69-7;(S)-Ethyl 3-amino-3-phenylpropanoate;ethyl (3S)-3-amino-3-phenylpropanoate;Ethyl (S)-3-amino-3-phenylpropanoate;(betaS)-beta-Aminobenzenepropanoic Acid Ethyl Ester;Benzenepropanoic acid, beta-amino-, ethyl ester, (betaS)-;(S)-ETHYL3-AMINO-3-PHENYLPROPANOATE;SCHEMBL1143911;d-beta-phenylalanine ethyl ester;DTXSID80358773;(s)-beta-phenylalanine ethyl ester;ethyl(S)-3-amino-3-phenylpropanoate;MFCD06761763;ethyl (S)-3-amino-3-phenylpropionate;(3S)-3-Phenyl-beta-alanine ethyl ester;(S)-3-Amino-3-phenylpropionicacid,ethylester;EN300-66418;J-018158

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

Chemical Property:

• Boiling Point: 140-150 °C(Press: 16 Torr)
• 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(protect from light)
• 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:

99% ^*data from raw suppliers

(βS)-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: (βS)-β-Aminobenzenepropanoic Acid Ethyl Ester in the synthesis of CCR5 antagonists in the treatment of HIV. In addition, it is used in the preparation of 1,4-Benzoxazin-3(4H)-one derivatives showing antithrombotic activity.

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

There total 14 articles about (S)-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: 98.0%

ethanol (64-17-5) + (S)-(-)-β-Phenyl-β-alanine hydrochloride (83649-47-2) → ethyl (3S)-3-amino-3-phenylpropionate (3082-69-7)

Guidance literature:

With thionyl chloride; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.202007005

Reference yield: 83.1%

ethyl 3-amino-3-phenylacrylate methanesulfonate (650601-35-7) → ethyl (3S)-3-amino-3-phenylpropionate (3082-69-7) + (R)-3-amino-3-phenylpropionic acid ethyl ester (3082-68-6)

Guidance literature:

With hydrogen; In ethanol; at 50 ℃; for 15h; under 22502.3 Torr; Product distribution / selectivity;

Reference yield: 73.0%

(S)-ethyl 3-((R)-1,1-dimethylethylsulfinamido)-3-phenylpropanoate (1169704-19-1) → ethyl (3S)-3-amino-3-phenylpropionate (3082-69-7)

Guidance literature:

With hydrogenchloride; In diethyl ether; ethanol; at 20 ℃; for 0.5h;

DOI:10.1055/s-0028-1087964

upstream raw materials:

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

(R)-ethyl 3-(N-benzyl-N-((R)-1-phenylethyl)amino)-3-phenylpropanoate

3-amino-3-phenylpropionic acid ethyl ester

Downstream raw materials:

N-{(1S)-3-[methoxy(methyl)amino]-3-oxo-1-phenylpropyl}cyclobutanecarboxamide

tert-butyl {(1S)-3-[methoxy(methyl)amino]-3-oxo-1-phenylpropyl}carbamate

tert-butyl ((1S)-3-oxo-1-phenylbutyl)carbamate

Refernces

• 1、 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.
• 2、 Grayson, J. Ian,Roos, Juergen,Osswald, Steffen. "Development of a commercial process for (S)-β-phenylalanine (1)". scheme or table. p. 1201 - 1206. Retrieved 2011/12/16.