(αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid

Base Information

• Chemical Name: (αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid
• CAS No.: 223526-67-8
• Molecular Formula: C₂₀H₂₈FNO₅
• Molecular Weight: 381.444
• Mol file: 223526-67-8.mol

Synonyms:(2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid

Chemical Property of (αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid

Chemical Property:

• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

(αR)-α-[(3S)-3-(tert-Butyloxycarbonylamino)-4-methyl-2-oxopentyl]-4-fluoro-benzenepropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid can be used in the preparation of rhinovirus protease inhibitors and peptidomimetic α,β-unsaturated esters.

Technology Process of (αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid

There total 33 articles about (αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid 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: 90.0%

(2R,5S)-methyl 5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate (862414-80-0) → (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid (223526-67-8)

Guidance literature:

With lithium hydroxide; In methanol; water; at 0 ℃; for 1h;

DOI:10.1016/j.bmc.2005.05.065

Reference yield:

(R)-4-fluorophenylalanine (18125-46-7) → (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid (223526-67-8)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogen bromide; sodium nitrite / 11 h / 0 - 20 °C

2: sulfuric acid / 2 h / 70 °C

3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 8 h / 80 °C

4: trifluoroacetic acid / dichloromethane / 4 h / 30 °C

5: palladium on activated charcoal; hydrogen / methanol / 25 °C

6: triethylamine / 2 h

7: sodium hydroxide / ethanol; water / 1 h / 20 °C

With sulfuric acid; palladium on activated charcoal; hydrogen bromide; hydrogen; potassium carbonate; triethylamine; trifluoroacetic acid; potassium iodide; sodium hydroxide; sodium nitrite; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1007/s11426-011-4478-5

Reference yield:

(2R,4S,5S)-5-tert-Butoxycarbonylamino-2-(4-fluoro-benzyl)-4-hydroxy-6-methyl-heptanoic acid → (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid (223526-67-8)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 23 ℃; for 1.33h;

DOI:10.1021/jm980537b

upstream raw materials:

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

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

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

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

Downstream raw materials:

ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate

ethyl-3--L-Phe(4-F)-L-(Tr-Gln)>-E-propenoate

(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

ethyl-3--L-Phe(4-F)-L-(Tr-Gln)>-E-propenoate

Refernces

• 1、 Shie, Jiun-Jie,Fang, Jim-Min,Kuo, Tun-Hsun,Kuo, Chih-Jung,Liang, Po-Huang,Huang, Hung-Jyun,Wu, Yin-Ta,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Wong, Chi-Huey. "Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters". . p. 5240 - 5252. Retrieved 2007/10/03.
• 2、 Dragovich, Peter S.,Prins, Thomas J.,Zhou, Ru,Fuhrman, Shella A.,Patick, Amy K.,Matthews, David A.,Ford, Clifford E.,Meador III, James W.,Ferre, Rose Ann,Worland, Stephen T.. "Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics". . p. 1203 - 1212. Retrieved 2007/10/03.