Ethyl (R)-2-Hydroxy-4-phenylbutyrate

Base Information

• Chemical Name: Ethyl (R)-2-Hydroxy-4-phenylbutyrate
• CAS No.: 90315-82-5
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Hs Code.: 29181990
• European Community (EC) Number: 618-525-4
• UNII: QP7IWH2QOX
• DSSTox Substance ID: DTXSID20370015
• Nikkaji Number: J275.578E
• ChEMBL ID: CHEMBL4630646
• Mol file: 90315-82-5.mol

Synonyms:(R)-HPBE;ethyl (R)-2-hydroxy-4-phenylbutyrate

Chemical Property of Ethyl (R)-2-Hydroxy-4-phenylbutyrate

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 6.44E-05mmHg at 25°C
• Melting Point: NA
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 330.9 °C at 760 mmHg
• PKA: 13.00±0.20(Predicted)
• Flash Point: 137.6 °C
• PSA: 46.53000
• Density: 1.098 g/cm³
• LogP: 1.54320
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 185

Purity/Quality:

99%, ^*data from raw suppliers

(R)-2-Hydroxy-4-phenylbutyricAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)O
• Isomeric SMILES: CCOC(=O)[C@@H](CCC1=CC=CC=C1)O
• Uses: Ethyl(R)-2-hydroxy-4-phenylbutyrate is used in the preparation of benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia. Ethyl (R)-(?)-2-hydroxy-4-phenylbutyrate can be used as a key intermediate for the synthesis of various ACE inhibitors like Cilazapril, Benazepril, and Enalapril.

Technology Process of Ethyl (R)-2-Hydroxy-4-phenylbutyrate

There total 63 articles about Ethyl (R)-2-Hydroxy-4-phenylbutyrate 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%

ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate (244277-48-3) → ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 5.5h; under 825.066 Torr;

DOI:10.1016/S0040-4020(00)00617-7

Reference yield: 98.0%

ethanol (64-17-5) + (R)-2-hydroxy4-phenylbutanoic acid (29678-81-7,111611-91-7) → ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5)

Guidance literature:

With sulfuric acid; for 16h; Ambient temperature;

DOI:10.1021/jm00394a009

Reference yield: 98.0%

ethanol (64-17-5) + ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate (244277-48-3) → ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; at 40 ℃; under 825.066 Torr;

DOI:10.1055/s-2003-40885

upstream raw materials:

ethanol

(R)-2-hydroxy4-phenylbutanoic acid

(Z)-(R)-4-Chloro-1-phenyl-hept-4-en-3-ol

ethyl 2-hydroxy-4-phenylbutanoate

Downstream raw materials:

benazepril hydrochloride

(2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester

(1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate

(2R)-4-phenylbutane-1,2-diol

Refernces

• 1、 Chadha,Manohar,Soundararajan,Lokeswari. "Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures". . p. 1571 - 1572. Retrieved 1996.
• 2、 de Gonzalo, Gonzalo. "Biocatalysed reductions of α-ketoesters employing CyreneTM as cosolvent". . . Retrieved 2021/02/26.
• 3、 Eskici, Mustafa,Karanfil, Abdullah,?zer, M. Sabih,Kabak, Yal??n,Durucasu, ?nci. "Asymmetric synthesis of (S)-dihydrokavain from l-malic acid". . p. 2382 - 2390. Retrieved 2018/10/20.