Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate

Base Information

• Chemical Name: Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate
• CAS No.: 88767-98-0
• Molecular Formula: C13H15F3O5S
• Molecular Weight: 340.32
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID10446233
• Wikidata: Q72476791
• Mol file: 88767-98-0.mol

Synonyms:Benzenebutanoicacid, a-[[(trifluoromethyl)sulfonyl]oxy]-,ethyl ester, (R)-;Ethyl (R)-2-hydroxy-4-phenylbutyrate triflate;Ethyl (R)-[a-(trifluoromethylsulfonyl)oxy]benzenebutanoate;Ethyl 2(R)-[(trifluoromethylsulfonyl)oxy]-4-phenylbutyrate;Ethyl2-(R)-trifluoromethanesulfonyloxy-4-phenylbutanoate;alpha-[[(Trifluoromethyl)sulfonyl]oxy]-benzenebutanoic acid ethyl ester;

Chemical Property of Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.482
• Boiling Point: 390.81 °C at 760 mmHg
• Flash Point: 190.155 °C
• PSA: 78.05000
• Density: 1.348 g/cm³
• LogP: 3.49790
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 340.05922923
• Heavy Atom Count: 22
• Complexity: 449

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl(R)-2-Hydroxy-4-phenylbutyrateTriflate ^*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)OS(=O)(=O)C(F)(F)F
• Isomeric SMILES: CCOC(=O)[C@@H](CCC1=CC=CC=C1)OS(=O)(=O)C(F)(F)F
• Uses: Ethyl (R)?-?4-?Phenyl-?2-?[[(trifluoromethyl)?sulfonyl]?oxy]?butyrate is an intermediate in synthesizing Enalapril-d3 Hydrochloride (E555258), which is the hydrochloride salt of Enalapril-d3 (E555253), a labeled version of Enalapril (E555403), an antihypertensive that is also an angiotensin-converting enzyme (ACE) inhibitor.

Technology Process of Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate

There total 5 articles about Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate 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: 100.0%

trifluoromethylsulfonic anhydride (358-23-6) + ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate (88767-98-0,138333-09-2)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jm00394a009

Reference yield:

(E)-2-oxo-4-phenyl-3-butenoic acid (1914-59-6) → ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate (88767-98-0,138333-09-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / p-toluenesulfonic acid*H₂O / benzene / 5 h / Heating

2: 29 percent / H₂ / 5percent Pd/C / propan-2-ol / 5 h / 50 °C / 2280 Torr

3: 86 percent / KOH / ethanol / 16 h / Ambient temperature

4: 98 percent / conc. H₂SO₄ / 16 h / Ambient temperature

5: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; potassium hydroxide; sulfuric acid; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1021/jm00394a009

Reference yield:

2-oxo-4-phenylbut-3-enoic acid 2-isopropyl-5-methylcyclohexyl ester (110143-65-2) → ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate (88767-98-0,138333-09-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 29 percent / H₂ / 5percent Pd/C / propan-2-ol / 5 h / 50 °C / 2280 Torr

2: 86 percent / KOH / ethanol / 16 h / Ambient temperature

3: 98 percent / conc. H₂SO₄ / 16 h / Ambient temperature

4: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; potassium hydroxide; sulfuric acid; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1021/jm00394a009

upstream raw materials:

trifluoromethylsulfonic anhydride

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

(E)-2-oxo-4-phenyl-3-butenoic acid

R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

Downstream raw materials:

Benzyl (2S)-2-amino>propionate

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

(3S,1'S)-ethyl-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetate

(S)-2-((2R,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

Refernces

• 1、 -. "ENALAPRIL-NITROXYDERIVATIVES DERIVATIVES AND RELATED COMPOUNDS AS ACE INHIBITORS FOR THE TREATMENT OF CARDIOVASCULAR DISEASES". Page 70. . Retrieved 2008/06/13.
• 2、 Yanagisawa, Hiroaki,Ishihara, Sadao,Ando, Akiko,Kanazaki, Takuro,Miyamoto, Shuichi,et al.. "Angiotensin-Converting Enzyme Inhibitors: Perhydro-1,4-thiazepin-5-one Derivatives". . p. 1984 - 1991. Retrieved 2007/10/02.