N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide

Base Information

• Chemical Name: N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide
• CAS No.: 103580-40-1
• Molecular Formula: C₂₇H₃₅ClN₆O₉S₂
• Molecular Weight: 687.195
• Mol file: 103580-40-1.mol

Synonyms:

Chemical Property of N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide

There total 6 articles about N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide 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:

N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline ethyl ester S,S-dioxide (103580-39-8,103665-10-7) → N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide (103580-40-1,103665-11-8,103665-13-0)

Guidance literature:

With sodium hydroxide; In ethanol;

DOI:10.1021/jm00168a013

Reference yield:

N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-N-(2,2,2-trichloroethoxycarbonyl)-L-alanine (92893-50-0) → N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide (103580-40-1,103665-11-8,103665-13-0)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 3.5 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / Ambient temperature

3: 95 percent / pyridinium chlorochromate / CH₂Cl₂ / 72 h / Ambient temperature

4: Zn, HOAc / ethanol / Ambient temperature

5: 1.) DMF, MgSO₄, 2.) NaBCNH₃ / 1.) RT, 30 min, 2.) overnight

6: aq. NaOH / ethanol

With sodium hydroxide; oxalyl dichloride; sodium cyanoborohydride; magnesium sulfate; acetic acid; triethylamine; N,N-dimethyl-formamide; pyridinium chlorochromate; zinc; In ethanol; dichloromethane;

DOI:10.1021/jm00168a013

Reference yield:

(S)-2-[((S)-1-Chlorocarbonyl-ethyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-4-phenyl-butyric acid ethyl ester (92893-51-1) → N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline S,S-dioxide (103580-40-1,103665-11-8,103665-13-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / Ambient temperature

2: 95 percent / pyridinium chlorochromate / CH₂Cl₂ / 72 h / Ambient temperature

3: Zn, HOAc / ethanol / Ambient temperature

4: 1.) DMF, MgSO₄, 2.) NaBCNH₃ / 1.) RT, 30 min, 2.) overnight

5: aq. NaOH / ethanol

With sodium hydroxide; sodium cyanoborohydride; magnesium sulfate; acetic acid; triethylamine; N,N-dimethyl-formamide; pyridinium chlorochromate; zinc; In ethanol; dichloromethane;

DOI:10.1021/jm00168a013

upstream raw materials:

N--L-alanyl>-(4RS)-4--N-methylamino>-L-proline ethyl ester S,S-dioxide

N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-N-(2,2,2-trichloroethoxycarbonyl)-L-alanine

(S)-2-[((S)-1-Chlorocarbonyl-ethyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-4-phenyl-butyric acid ethyl ester

N--N'-<(2,2,2-trichloroethoxy)carbonyl>-L-alanyl>-L-prolin-4-one ethyl ester