(S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
• CAS No.: 117605-22-8
• Molecular Formula: C₂₄H₃₅N₃O₆
• Molecular Weight: 461.558
• Mol file: 117605-22-8.mol

Synonyms:(S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester

Chemical Property of (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester

There total 12 articles about (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic 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: 52.8%

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride (90891-21-7) + tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate (195828-75-2) → (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester (117605-22-8)

Guidance literature:

With potassium carbonate; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 48h; Ambient temperature;

DOI:10.1021/jm00122a003

Reference yield: 52.8%

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride (90891-21-7) + 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-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89371-38-0) + (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester (117605-22-8)

Guidance literature:

With potassium carbonate; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 48h; Ambient temperature;

DOI:10.1021/jm00122a003

Reference yield:

2-bromo-4-phenyl butanoic acid (16503-46-1) → (S)-3-[(R)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester (117605-22-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 28percent aq. NH₃ / 168 h / Ambient temperature

3: CoCl₂ / H₂O / 72 h / 37 °C / aminoacylase (from Aspergillus oryzae); pH 7

4: SOCl₂

5: 27.8 percent / K₂CO₃ / dimethylsulfoxide / 30 h / Ambient temperature

6: ethanolic HCl

7: 95.1 percent / H₂ / Pd / ethanol / 3 h / 760 Torr / Ambient temperature

8: DCC / tetrahydrofuran / Ambient temperature

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

With hydrogenchloride; ammonium hydroxide; thionyl chloride; potassium tert-butylate; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide;

DOI:10.1021/jm00122a003

upstream raw materials:

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

tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate

2-bromo-4-phenyl butanoic acid

D,L-homophenylalanine

Downstream raw materials:

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