(3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone

Base Information

• Chemical Name: (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone
• CAS No.: 127231-43-0
• Molecular Formula: C₃₂H₄₂ClN₅O₇
• Molecular Weight: 644.168
• Mol file: 127231-43-0.mol

Synonyms:(3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone

Chemical Property of (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone

There total 9 articles about (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone 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:

(S)-2-[(S)-2-((S)-2-Amino-3-benzyloxy-propionylamino)-4-methyl-pentanoylamino]-N1-((S)-1-benzyl-3-chloro-2-oxo-propyl)-succinamide + acetyl chloride (75-36-5) → (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone (127231-43-0)

Guidance literature:

With 4-methyl-morpholine;

DOI:10.1021/jm00167a003

Reference yield:

(S)-2-Amino-N1-((S)-1-benzyl-3-chloro-2-oxo-propyl)-succinamide → (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone (127231-43-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight

2: 4 N HCl / dioxane / 1 h / Ambient temperature

3: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight

4: 4 N HCl / dioxane / 1 h / Ambient temperature

5: triethylamine, DCM / dimethylformamide / 2 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; benzotriazol-1-ol; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00099a008

Reference yield:

(S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-N1-((S)-1-benzyl-3-chloro-2-oxo-propyl)-succinamide → (3S)-<(N-acetyl-O-benzylserinylleucinylasparaginyl)amino>-1-chloro-4-phenyl-2-butanone (127231-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight

2: 4 N HCl / dioxane / 1 h / Ambient temperature

3: triethylamine, DCM / dimethylformamide / 2 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; benzotriazol-1-ol; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00099a008

upstream raw materials:

acetyl chloride

N-tert-butoxycarbonyl-L-phenylalanine

(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate

(3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride

Downstream raw materials:

C₄₉H₇₂N₈O₁₁

Ac-Ser-Leu-Asn--Ile-Val-OMe

(2R/S,3S)-3-<(N-acetylserinylleucinylasparaginyl)amino>-2-hydroxy-4-phenyl-1-(N-prolylisoleucinylphenylalanine methyl ester)butane

C₄₇H₇₀N₈O₁₁