[(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

Base Information

• Chemical Name: [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone
• CAS No.: 642478-89-5
• Molecular Formula: C₂₄H₃₁N₃O₅S₂
• Molecular Weight: 505.659
• Mol file: 642478-89-5.mol

Synonyms:[(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

Chemical Property of [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

There total 5 articles about [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone 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: 72.0%

[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone (642478-88-4) → [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone (642478-89-5)

Guidance literature:

With ammonium hydroxide; thiamine diphosphate; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone (642478-89-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / SOCl₂; H₂O / benzene / 2 h / 20 °C

2: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

3: 70 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 62 percent / TMSCl / CH₂Cl₂ / 8 h / 20 °C

5: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

6: 76 percent / NaN₃ / dimethylformamide / 16 h / 60 °C

7: 72 percent / TPP; aq. NH₃ / tetrahydrofuran / 8 h / 20 °C

With 1H-imidazole; ammonium hydroxide; chloro-trimethyl-silane; thionyl chloride; sodium azide; TEA; water; thiamine diphosphate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate (382137-65-7) → [(2S,4S)-4-Amino-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone (642478-89-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

2: 70 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

3: 62 percent / TMSCl / CH₂Cl₂ / 8 h / 20 °C

4: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

5: 76 percent / NaN₃ / dimethylformamide / 16 h / 60 °C

6: 72 percent / TPP; aq. NH₃ / tetrahydrofuran / 8 h / 20 °C

With 1H-imidazole; ammonium hydroxide; chloro-trimethyl-silane; sodium azide; TEA; thiamine diphosphate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2003.08.071

upstream raw materials:

[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

L-4-hydroxyproline methyl ester hydrochloride

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate

(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

Downstream raw materials:

N-[(3S,5S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-butyramide

5-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentanoic acid [(3S,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide

5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid [(3S,5S)-1-(2-amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-amide

N-[(3S,5S)-1-(2-Amino-4-benzyloxy-5-methoxy-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl]-4-{5-amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-butyramide