tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

Base Information

• Chemical Name: tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate
• CAS No.: 307304-62-7
• Molecular Formula: C₂₀H₂₉N₃O₄
• Molecular Weight: 375.468
• Mol file: 307304-62-7.mol

Synonyms:tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

Chemical Property of tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

There total 5 articles about tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate 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:

(4R,5S)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (112791-04-5) → tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate (307304-62-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetonitrile / 4 h / 80 °C

2.1: NaN₃ / acetonitrile / 72 h / 80 °C

3.1: H₂; HCl / Pd/C / methanol; H₂O

4.1: CH₂Cl₂ / 24 h / 20 °C

5.1: DBU; LiCl / acetonitrile / 12 h / -20 °C

5.2: HCl / H₂O

With hydrogenchloride; sodium azide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; water; acetonitrile; 1.1: Substitution / 2.1: Substitution / 3.1: Catalytic hydrogenation / 4.1: Condensation / 5.1: Addition / 5.2: Hydrolysis;

DOI:10.1021/jo000321t

Reference yield:

(4R,5S)-(+)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone (143359-25-5) → tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate (307304-62-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaN₃ / acetonitrile / 72 h / 80 °C

2.1: H₂; HCl / Pd/C / methanol; H₂O

3.1: CH₂Cl₂ / 24 h / 20 °C

4.1: DBU; LiCl / acetonitrile / 12 h / -20 °C

4.2: HCl / H₂O

With hydrogenchloride; sodium azide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; water; acetonitrile; 1.1: Substitution / 2.1: Catalytic hydrogenation / 3.1: Condensation / 4.1: Addition / 4.2: Hydrolysis;

DOI:10.1021/jo000321t

Reference yield:

(4R,5S)-(+)-1-(2'-azidoacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone → tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate (307304-62-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂; HCl / Pd/C / methanol; H₂O

2.1: CH₂Cl₂ / 24 h / 20 °C

3.1: DBU; LiCl / acetonitrile / 12 h / -20 °C

3.2: HCl / H₂O

With hydrogenchloride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; water; acetonitrile; 1.1: Catalytic hydrogenation / 2.1: Condensation / 3.1: Addition / 3.2: Hydrolysis;

DOI:10.1021/jo000321t

upstream raw materials:

tert-Butyl acrylate

(4R,5S)-(+)-1-[2'-(diphenylmethyleneamino)acetyl]-3,4-dimethyl-5-phenyl-2-imidazolidinone

(4R,5S)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

(4R,5S)-(+)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone

Downstream raw materials:

D-pyrrolidone-5-carboxylic acid

Refernces