(2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide

Base Information

• Chemical Name: (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide
• CAS No.: 454482-19-0
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.353
• Mol file: 454482-19-0.mol

Synonyms:

Chemical Property of (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide

There total 3 articles about (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide 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:

2-Methyl-4-((S)-1-phenyl-ethylcarbamoyl)-pentanoic acid → (2R,4S)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide + (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide (454482-19-0)

Guidance literature:

With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; diethyl ether; at -20 - 20 ℃; for 1.25h;

DOI:10.1055/s-2002-28510

Reference yield:

(3R,5S)-3,5-dimethyldihydro-2H-pyran-2,6(3H)-dione (4295-92-5) → (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide (454482-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 16.33 h / 0 - 20 °C

2: 9.55 g / BF₃*THF / tetrahydrofuran; diethyl ether / 1.25 h / -20 - 20 °C

With pyridine; boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1055/s-2002-28510

Reference yield:

pentane-2,2,4-tricarboxylic acid-2,2-diethyl ester-4-methyl ester (342806-74-0) → (2S,4R)-5-hydroxy-2,4-dimethyl-N-[(S)-1-phenylethyl]pentanamide (454482-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: glacial HOAc; aq. HCl / 25 h / Heating

2: 98.1 g / Ac₂O / 1.5 h

3: pyridine / CH₂Cl₂ / 16.33 h / 0 - 20 °C

4: 9.55 g / BF₃*THF / tetrahydrofuran; diethyl ether / 1.25 h / -20 - 20 °C

With pyridine; hydrogenchloride; boron trifluoride-tetrahydrofuran complex; acetic anhydride; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1055/s-2002-28510

upstream raw materials:

(3R,5S)-3,5-dimethyldihydro-2H-pyran-2,6(3H)-dione

pentane-2,2,4-tricarboxylic acid-2,2-diethyl ester-4-methyl ester

Downstream raw materials:

(+)-(2S,4R)-cis-2,4-dimethyl-δ-valerolactone

Refernces