(2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Base Information

• Chemical Name: (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS No.: 343308-55-4
• Molecular Formula: C₂₀H₂₉BrN₂O₅S₂
• Molecular Weight: 521.497
• Mol file: 343308-55-4.mol

Synonyms:(2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property of (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 15 articles about (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-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: 96.0%

(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal (140647-02-5) + 1,3-dibromo-propane (109-64-8) → (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (343308-55-4)

Guidance literature:

With potassium carbonate; In acetone; for 48h; Reflux;

DOI:10.1016/j.ejmech.2010.05.041

Reference yield: 82.0%

ethanethiol (75-08-1) + (S)-1-[4-(3-Bromo-propoxy)-5-methoxy-2-nitro-benzoyl]-pyrrolidine-2-carbaldehyde (478552-08-8) → (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (343308-55-4)

Guidance literature:

With chloro-trimethyl-silane; In chloroform; at 20 ℃; for 18h;

DOI:10.1016/S0960-894X(02)00324-4

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → (2S)-N-[4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (343308-55-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / potassium carbonate / acetone / 48 h / Heating

2: 90 percent / stannic chloride; fuming nitric acid / CH₂Cl₂ / 0.08 h / -25 °C

3: 89 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O; methanol / 12 h / 20 °C

4: thionyl chloride; DMF / benzene / 6 h

5: 464 mg / triethylamine / tetrahydrofuran; H₂O

With lithium hydroxide; thionyl chloride; nitric acid; tin(IV) chloride; potassium carbonate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;

DOI:10.1016/j.bmc.2005.08.020

upstream raw materials:

(2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-pyrrole

ethanethiol

(S)-1-[4-(3-Bromo-propoxy)-5-methoxy-2-nitro-benzoyl]-pyrrolidine-2-carbaldehyde

4-hydroxy-3-methoxybenzoic acid methyl ester

Downstream raw materials:

(2S)-N-{4-[4-[3-[4-(2-oxo-2H-2-chromenyl)piperazino]propyl]oxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethylthioacetal

(2S)-N-{4-[3-(7-methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one-8-yloxy)propoxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carbaldehyde diethyl thioacetal

(2S)-N-{3-(4-[1H-benzo[d]imidazol-2-yl]phenoxy)propoxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

(2S)-N-{4-[3-(7-methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c]-[1,4]benzodiazepine-5,11-dione-8-yloxy)propoxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal