1-Methyl-2-oxo-3-[1-oxo-2-[[3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]propyl]-4-imidazolidinecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: 1-Methyl-2-oxo-3-[1-oxo-2-[[3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]propyl]-4-imidazolidinecarboxylic acid tert-butyl ester
• CAS No.: 89460-20-8
• Molecular Formula: C29H37N3O6
• Molecular Weight: 523.629
• DSSTox Substance ID: DTXSID70541773
• Mol file: 89460-20-8.mol

Synonyms:89460-20-8;1-METHYL-2-OXO-3-[1-OXO-2-[[3-PHENYL-1-[(PHENYLMETHOXY)CARBONYL]PROPYL]AMINO]PROPYL]-4-IMIDAZOLIDINECARBOXYLIC ACID TERT-BUTYL ESTER;tert-butyl 1-methyl-2-oxo-3-[2-[(1-oxo-4-phenyl-1-phenylmethoxybutan-2-yl)amino]propanoyl]imidazolidine-4-carboxylate;Imidaprilat Benzyl Ester, (Carbonylimidazolidine)tert-butyl Ester;DTXSID70541773;AKOS030243007;tert-Butyl 3-{N-[1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]alanyl}-1-methyl-2-oxoimidazolidine-4-carboxylate

Chemical Property of 1-Methyl-2-oxo-3-[1-oxo-2-[[3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]propyl]-4-imidazolidinecarboxylic acid tert-butyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 627.941°C at 760 mmHg
• Flash Point: 333.567°C
• PSA: 105.25000
• Density: 1.192g/cm³
• LogP: 3.58030
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 523.26823591
• Heavy Atom Count: 38
• Complexity: 829

Purity/Quality:

97% ^*data from raw suppliers

ImidaprilatBenzylEster,(Carbonylimidazolidine)tert-butylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1C(CN(C1=O)C)C(=O)OC(C)(C)C)NC(CCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3

Technology Process of 1-Methyl-2-oxo-3-[1-oxo-2-[[3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]propyl]-4-imidazolidinecarboxylic acid tert-butyl ester

There total 12 articles about 1-Methyl-2-oxo-3-[1-oxo-2-[[3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]propyl]-4-imidazolidinecarboxylic acid tert-butyl 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: 82.3%

tert-Butyl (4S)-1-Methyl-3-<(2R)-2-(4-toluenesulfonyloxy)propionyl>-2-oxoimidazolidine-4-carboxylate (130368-70-6) + benzyl (2S)-2-amino-4-phenylbutyrate (83080-02-8) → tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89460-20-8)

Guidance literature:

Reference yield:

benzyl (2S)-2-amino-4-phenylbutyrate (83080-02-8) + tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate (195828-75-2) → tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89460-20-8) + tert-butyl (4S)-3-<(2R)-2-propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate (89371-79-9)

Guidance literature:

With potassium carbonate; In N,N,N,N,N,N-hexamethylphosphoric triamide;

Reference yield:

(S)‐2‐oxoimidazolidine‐1,5‐dicarboxylate-5‐tert‐butyl ester-1‐benzyl ester (77999-24-7) → tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89460-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89.8 percent / K₂CO₃ / acetone / 72 h / Ambient temperature

2: 98.2 percent / H₂ / Pd / methanol / 3 h / 760 Torr / Ambient temperature

3: 1) tBuOK / 1) THF, -50 deg C, 20 min, 2) THF, -30 deg C, 20 min

With potassium tert-butylate; hydrogen; potassium carbonate; palladium; In methanol; acetone;

DOI:10.1021/jm00122a003

upstream raw materials:

tert-Butyl (4S)-1-Methyl-3-<(2R)-2-(4-toluenesulfonyloxy)propionyl>-2-oxoimidazolidine-4-carboxylate

benzyl (2S)-2-amino-4-phenylbutyrate

2-bromo-4-phenyl butanoic acid

D,L-homophenylalanine

Downstream raw materials:

tert-butyl (4S)-3-<(2S)-2-propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate hydrogen maleate

(4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid