(4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid

Base Information

• Chemical Name: (4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid
• CAS No.: 1026773-47-6
• Molecular Formula: C₂₈H₃₁NO₄
• Molecular Weight: 445.558
• Mol file: 1026773-47-6.mol

Synonyms:(4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid

Chemical Property of (4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid

There total 2 articles about (4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic 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: 50.0%

(R)-N-benzyl-1-phenylethylamine (38235-77-7) + Methyl 3-acetoxy-2-methylene-3-phenylpropanoate (124957-36-4) → C26H27NO2 + (4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid (1026773-47-6) + (4R,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid + C41H44N2O2 + C41H44N2O2 (1026773-57-8)

Guidance literature:

(R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

Methyl 3-acetoxy-2-methylene-3-phenylpropanoate; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; at -78 - 20 ℃; optical yield given as %de;

DOI:10.1021/ol8001464

Reference yield: 3.0%

(R)-N-benzyl-1-phenylethylamine (38235-77-7) + methyl 2-(acetoxymethyl)-3-phenylprop-2-enoate (1026773-42-1) → C26H27NO2 + (4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid (1026773-47-6) + (4R,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid + C41H44N2O2 (1026773-57-8)

Guidance literature:

(R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl 2-(acetoxymethyl)-3-phenylprop-2-enoate; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; at -78 - 20 ℃; optical yield given as %de;

DOI:10.1021/ol8001464

Reference yield: 81.0%

(4S,5S,αR)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-5-phenyl-pentanoic acid (1026773-47-6) → (5S,6S)-5-methoxycarbonyl-6-phenyl-piperidin-2-one (1026773-67-0)

Guidance literature:

With 10% Pd/C; hydrogen; acetic acid; at 20 ℃; for 23h; under 3800.26 Torr;

DOI:10.1021/ol8001464

upstream raw materials:

(R)-N-benzyl-1-phenylethylamine

Methyl 3-acetoxy-2-methylene-3-phenylpropanoate

methyl 2-(acetoxymethyl)-3-phenylprop-2-enoate

Downstream raw materials:

(5S,6S)-5-methoxycarbonyl-6-phenyl-piperidin-2-one