(S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester

Base Information

• Chemical Name: (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester
• CAS No.: 109801-68-5
• Molecular Formula: C₂₁H₂₈ClNO₆
• Molecular Weight: 425.909
• Mol file: 109801-68-5.mol

Synonyms:(S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester

Chemical Property of (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester

There total 9 articles about (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl 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: 87.0%

N-<(S)-4-hydroxy-5-methyl-3-oxohexanoyl>-L-leucine p-chlorophenacyl ester (109801-82-3) + 4-chlorobenzoylmethyl bromide (536-38-9) → (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester (109801-68-5)

Guidance literature:

With potassium hydrogencarbonate; In acetone; for 3.5h; Heating;

DOI:10.1021/jo00229a019

Reference yield:

(S)-4-<(isobutoxycarbonyl)oxy>-5-methyl-3-oxohexanoic acid ethyl thio ester (109801-91-4) → (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester (109801-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / triethylamine, cuprous iodide / CH₂Cl₂ / Ambient temperature

2: 97 percent / NaOH / diethyl ether / 1 h / Ambient temperature

3: 87 percent / KHCO₃ / acetone / 3.5 h / Heating

With sodium hydroxide; copper(l) iodide; potassium hydrogencarbonate; triethylamine; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00229a019

Reference yield:

C15H26O7 (109801-88-9) → (S)-2-((S)-4-Hydroxy-5-methyl-3-oxo-hexanoylamino)-4-methyl-pentanoic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester (109801-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) diisopropylamine, n-BuLi / 1.) THF, -70 deg C, 30 min, 2.) THF, -65 deg C, 20 min

2: 68 percent / triethylamine, cuprous iodide / CH₂Cl₂ / Ambient temperature

3: 97 percent / NaOH / diethyl ether / 1 h / Ambient temperature

4: 87 percent / KHCO₃ / acetone / 3.5 h / Heating

With sodium hydroxide; copper(l) iodide; n-butyllithium; potassium hydrogencarbonate; triethylamine; diisopropylamine; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00229a019

upstream raw materials:

N-<(S)-4-hydroxy-5-methyl-3-oxohexanoyl>-L-leucine p-chlorophenacyl ester

4-chlorobenzoylmethyl bromide

2,2-Dimethyl-propionic acid (S)-3-ethylsulfanylcarbonyl-1-isopropyl-2-oxo-propyl ester

(S)-4-<(isobutoxycarbonyl)oxy>-5-methyl-3-oxohexanoic acid ethyl thio ester