(2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester

Base Information

• Chemical Name: (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester
• CAS No.: 328273-04-7
• Molecular Formula: C₁₁H₁₀F₄O₅S
• Molecular Weight: 330.257
• Mol file: 328273-04-7.mol

Synonyms:(2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester

Chemical Property of (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester

There total 2 articles about (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester 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:

(R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate (124980-98-9) + 2,6-dimethylpyridine (108-48-5) → (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester (328273-04-7)

Guidance literature:

With hydrogenchloride; trifluoromethanesulfonic acid anhydride; In dichloromethane;

Reference yield:

(R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate (124980-98-9) + trifluoromethylsulfonic anhydride (358-23-6) → (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester (328273-04-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1016/j.bmc.2005.05.065

Reference yield:

(2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester (328273-04-7) → (2R,5S)-2-(4-Fluoro-benzyl)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-4-oxo-heptanoic acid (328086-55-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: tetrahydrofuran / 24 h / 0 - 20 °C

2.1: CF₃CO₂H / CH₂Cl₂ / 24 h / 20 °C

3.1: 83 percent / H₂ / Pd-C / methanol / 10 h / 20 °C

4.1: 90 percent / lithium hydroxide / H₂O; methanol / 1 h / 0 °C

5.1: 84 percent / Cs₂CO₃ / dimethylformamide / 5 h / 45 °C

6.1: HCl / dioxane / 2 h / 20 °C

7.1: 187 mg / 4-methylmorpholine / CH₂Cl₂ / 2 h / 25 °C

8.1: 85 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 25 °C

With morpholine; 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; hydrogen; sodium hydride; caesium carbonate; trifluoroacetic acid; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.05.065

upstream raw materials:

(R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate

trifluoromethylsulfonic anhydride

2,6-dimethylpyridine

Downstream raw materials:

(2R,5S)-2-(4-Fluoro-benzyl)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-4-oxo-heptanoic acid

(2R,5S)-methyl 5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate

(2R,5S)-methyl 5-(benzyloxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate

allyl (2R,5S)-5-(tert-butoxycarbonyl)amino-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate

Refernces

• 1、 -. "Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis". . . Retrieved 2008/06/13.