Ethyl (alphaS)-alpha-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]benzenebutanoate

Base Information

• Chemical Name: Ethyl (alphaS)-alpha-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]benzenebutanoate
• CAS No.: 82717-95-1
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.461
• DSSTox Substance ID: DTXSID701135174
• Nikkaji Number: J1.631.095F
• Mol file: 82717-95-1.mol

Synonyms:SCHEMBL7343890;DTXSID701135174;82717-95-1;Ethyl (alphaS)-alpha-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]benzenebutanoate

Chemical Property of Ethyl (alphaS)-alpha-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]benzenebutanoate

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 369.19400834
• Heavy Atom Count: 27
• Complexity: 442

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)OCC2=CC=CC=C2

Technology Process of Ethyl (alphaS)-alpha-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]benzenebutanoate

There total 19 articles about Ethyl (alphaS)-alpha-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]benzenebutanoate 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: 75.0%

ethyl 2-amino-4-phenyl-(2S)-butyrate (46460-23-5) + Benzyl (2R)-2-(4-toluenesulfonyloxy)propionate (117589-36-3) → Benzyl (2S)-2-amino>propionate (82717-95-1)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; at 65 ℃; for 24h;

DOI:10.1248/cpb.39.1374

Reference yield: 27.8%

benzyl 2-bromopropionate (3017-53-6) + L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride (90891-21-7) → Benzyl (2S)-2-amino>propionate (82717-95-1) + benzyl (2R)-2-amino>propionate (93841-86-2)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; for 30h; Ambient temperature;

DOI:10.1021/jm00122a003

Reference yield: 15.9%

H-Ala-OBzl (17831-01-5) + ethyl 2-bromo-4-phenylbutanoate (82586-61-6) → Benzyl (2S)-2-amino>propionate (82717-95-1) + N-<1(R)-(Ethoxycarbonyl)-3-phenylpropyl>-(S)-alanin-benzylester (93841-86-2)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; for 30h; Ambient temperature;

DOI:10.1021/jm00122a003

upstream raw materials:

benzyl 2-bromopropionate

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride

H-Ala-OBzl

ethyl 2-bromo-4-phenylbutanoate

Downstream raw materials:

(2S)-3-aza-4-(ethoxycarbonyl)-2-methyl-6-phenylhexanamide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

N-succinimidyl (2S)-2-{N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propionate

benzyl (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate

(4S)-1-benzyl-3-<(2S)-2-amino>propionyl>-2-oxoimidazolidine-4-carboxylic acid

Refernces

• 1、 Baker, William R.,Fung, Anthony K. L.,Kleinert, Hollis D.,Stein, Herman H.,Plattner, Jacob J.,et al.. "Nonpeptide Renin Inhibitors Employing a Novel 3-Aza(or oxa)-2,4-dialkyl Glutaric Acid Moiety as a P2/P3 Amide Bond Replacement". . p. 1722 - 1734. Retrieved 2007/10/02.
• 2、 -. "Ophthalmic compositions". . . Retrieved 2008/06/13.