ethyl 4-fluoro-4-Methyl-2-pent-4-enaMidopentanoate

Base Information

• Chemical Name: ethyl 4-fluoro-4-Methyl-2-pent-4-enaMidopentanoate
• CAS No.: 848949-92-8
• Molecular Formula: C13H22FNO3
• Molecular Weight: 259.31700
• Mol file: 848949-92-8.mol

Synonyms:

Chemical Property of ethyl 4-fluoro-4-Methyl-2-pent-4-enaMidopentanoate

Chemical Property:

• PSA: 55.40000
• LogP: 2.52960

Purity/Quality:

≥95% ^*data from raw suppliers

L-Leucine,4-fluoro-N-(1-oxo-4-penten-1-yl)-,ethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-fluoro-4-Methyl-2-pent-4-enaMidopentanoate

There total 8 articles about ethyl 4-fluoro-4-Methyl-2-pent-4-enaMidopentanoate 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:

ethanol (64-17-5) + 2-but-3-enyl-4-(2-fluoro-2-methyl-propyl)-4H-oxazol-5-one (848949-90-6) → (S)-4-Fluoro-4-methyl-2-pent-4-enoylamino-pentanoic acid ethyl ester (848949-92-8)

Guidance literature:

With novozyme 435; triethylamine; In tert-butyl methyl ether; at 20 ℃; for 3 - 6h;

Reference yield:

ethanol (64-17-5) + 2-but-3-enyl-4-(2-fluoro-2-methyl-propyl)-4H-oxazol-5-one (848949-90-6) → (R)-4-Fluoro-4-methyl-2-pent-4-enoylamino-pentanoic acid ethyl ester + (S)-4-Fluoro-4-methyl-2-pent-4-enoylamino-pentanoic acid ethyl ester (848949-92-8)

Guidance literature:

With novozyme-435; triethylamine; In various solvent(s); at 20 ℃; for 4h; Title compound not separated from byproducts; Enzymatic reaction;

DOI:10.1021/jo047918j

Reference yield:

ethyl-2-(diphenylmethyleneamino)-4-fluoro-4-methylpentanoate (848949-86-0) → (S)-4-Fluoro-4-methyl-2-pent-4-enoylamino-pentanoic acid ethyl ester (848949-92-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HCl / H₂O; various solvent(s) / 12 h / 20 °C

1.2: NaHCO₃ / various solvent(s) / 0.5 h / 20 °C

1.3: 96 percent / NaOH / tetrahydrofuran; H₂O; various solvent(s) / 4 h / 20 °C

2.1: EDCI / CH₂Cl₂ / 2 h / 20 °C

3.1: Novozyme-435; Et₃N / various solvent(s) / 4 h / 20 °C / Enzymatic reaction

With hydrogenchloride; novozyme-435; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; water; 1.2: Schotten-Baumman rection;

DOI:10.1021/jo047918j

upstream raw materials:

ethanol

2-but-3-enyl-4-(2-fluoro-2-methyl-propyl)-4H-oxazol-5-one

pent-4-enoyl chloride

4-fluoro-4-methyl-2-pent-4-enoylamino-pentanoic acid

Downstream raw materials:

ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt

5-iodomethyl-dihydro-furan-2-one

ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate

5-bromomethyl-γ-butyrolactone

Refernces

• 1、 Limanto, John,Shafiee, Ali,Devine, Paul N.,Upadhyay, Veena,Desmond, Richard A.,Foster, Bruce R.,Gauthier Jr., Donald R.,Reamer, Robert A.,Volante. "An efficient chemoenzymatic approach to (S)-γ-fluoroleucine ethyl ester". . p. 2372 - 2375. Retrieved 2007/10/03.