(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

Base Information

• Chemical Name: (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS No.: 717920-70-2
• Molecular Formula: C₁₇H₂₃FN₂O₅S₂
• Molecular Weight: 418.51
• Mol file: 717920-70-2.mol

Synonyms:(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 4 articles about (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal 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: 75.0%

(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-69-9) → (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-70-2)

Guidance literature:

With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2004.02.063

Reference yield:

methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate (382137-65-7) → (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-70-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / DAST / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 85 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

3: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

4: 75 percent / EtSH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / 20 °C

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; diisobutylaluminium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; ethanethiol; In dichloromethane; chloroform;

DOI:10.1016/j.bmcl.2004.02.063

Reference yield:

(2S,4S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde (717920-68-8) → (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal (717920-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

2: 75 percent / EtSH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / 20 °C

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; chloroform;

DOI:10.1016/j.bmcl.2004.02.063

upstream raw materials:

(2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxaldehyde diethyl thioacetal

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

(2S,4S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-fluoro-pyrrolidine-2-carbaldehyde

methyl (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)-4-fluoropyrrolidine-2-carboxylate

Downstream raw materials:

1,1'-{[(propane-1,3-diyl)dioxy]bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoropyrrolidine-2-carboxaldehyde diethylthioacetal]

C₄₁H₄₂FN₇O₆S₂

C₄₂H₅₁FN₆O₉S₂

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