(R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester

Base Information

• Chemical Name: (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester
• CAS No.: 77982-73-1
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• Mol file: 77982-73-1.mol

Synonyms:(R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester

Chemical Property of (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester

There total 5 articles about (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl 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: 84.0%

3,3'-Dimethoxycarbonylpropanoic anhydride (52944-79-3) + N-benzoyl-2-phenylglycine (29670-63-1) → (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester (77982-73-1)

Guidance literature:

With pyridine; at 100 - 110 ℃; for 3h;

DOI:10.1055/s-1985-34141

Reference yield: 58.0%

diiodomethane (75-11-6) + (+/-)-methyl 4-(N-benzoyl)amino-3-oxo-5-phenylpentanoate → (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester (77982-73-1)

Guidance literature:

diiodomethane; With diethylzinc; In hexane; dichloromethane; at 0 ℃;

(+/-)-methyl 4-(N-benzoyl)amino-3-oxo-5-phenylpentanoate; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(03)00052-8

Reference yield:

2-Phenyl-4-benzyl-4-β-carbomethoxypropionyloxazolone (83084-67-7) → (R,S)-5-benzoylamino-4-oxo-6-phenylhexanoic acid methyl ester (77982-73-1)

Guidance literature:

With pyridine; acetic acid; at 100 ℃; for 1h;

DOI:10.1021/jm00353a005

upstream raw materials:

4-benzyl-2-phenyl-2-oxazolin-5-one

succinic acid monomethylester chloride

2-Phenyl-4-benzyl-4-β-carbomethoxypropionyloxazolone

3,3'-Dimethoxycarbonylpropanoic anhydride

Downstream raw materials:

(S)-1-((S)-5-Decanoylamino-4-oxo-6-phenyl-hexanoyl)-pyrrolidine-2-carboxylic acid

(S)-1-((S)-5-Octanoylamino-4-oxo-6-phenyl-hexanoyl)-pyrrolidine-2-carboxylic acid

5-n-butyloxycarbonylamino-4-oxo-6-phenylhexanoyl-L-proline

(S)-1-((S)-5-Hexanoylamino-4-oxo-6-phenyl-hexanoyl)-pyrrolidine-2-carboxylic acid

Refernces

• 1、 Theberge, Cory R.,Zercher, Charles K.. "Chain extension of amino acid skeletons: Preparation of ketomethylene isosteres". . p. 1521 - 1527. Retrieved 2007/10/03.
• 2、 Almquist,Crase,Jennings-White,Meyer,Hoefle,Smith,Essenburg,Kaplan. "Derivatives of the potent angiotensin converting enzyme inhibotor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline: Effect of changes at positions 2 and 5 of the hexanoic acid portion". . p. 1292 - 1299. Retrieved 2007/10/02.