(2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid
• CAS No.: 1448428-94-1
• Molecular Formula: C₂₀H₂₈FN₃O₇S
• Molecular Weight: 473.523
• Mol file: 1448428-94-1.mol

Synonyms:(2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid

Chemical Property of (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid

There total 6 articles about (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid 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: 54.7%

(2S,3S)-ethyl 3-((S)-1-(4-(4-fluorophenylsulfonamido)butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate (1448429-35-3) → (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid (1448428-94-1)

Guidance literature:

(2S,3S)-ethyl 3-((S)-1-(4-(4-fluorophenylsulfonamido)butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate; With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In water;

DOI:10.1021/jm4006719

Reference yield: 54.7%

→ (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid (1448428-94-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃;

Reference yield:

C10H15FN2O2S (1018514-38-9) → (2S,3S)-3-((S)-1-(4-(4-fluorophenylsulfonamido) butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid (1448428-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

2: trifluoroacetic acid / 6.5 h / 0 °C / Inert atmosphere

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere

4: lithium hydroxide / water; tetrahydrofuran; methanol / 3 h / 0 - 20 °C / Inert atmosphere

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm4006719

upstream raw materials:

C₁₀H₁₅FN₂O₂S

N-tert-butoxycarbonyl-L-leucine

C₂₁H₃₄FN₃O₅S

(2S,3S)-ethyl 3-((S)-1-(4-(4-fluorophenylsulfonamido)butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate

Refernces

• 1、 Schiefer, Isaac T.,Tapadar, Subhasish,Litosh, Vladislav,Siklos, Marton,Scism, Rob,Wijewickrama, Gihani T.,Chandrasena, Esala P.,Sinha, Vaishali,Tavassoli, Ehsan,Brunsteiner, Michael,Fa', Mauro,Arancio, Ottavio,Petukhov, Pavel,Thatcher, Gregory R. J.. "Design, synthesis, and optimization of novel epoxide incorporating peptidomimetics as selective calpain inhibitors". . p. 6054 - 6068. Retrieved 2013/09/02.