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

Base Information

• Chemical Name: (2S)-N-[5'-methoxy-4'-[(3''-methoxycarbonylpropyl)oxy]-2'-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS No.: 349536-25-0
• Molecular Formula: C₂₂H₃₂N₂O₇S₂
• Molecular Weight: 500.637
• Mol file: 349536-25-0.mol

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

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

There total 8 articles about (2S)-N-[5'-methoxy-4'-[(3''-methoxycarbonylpropyl)oxy]-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: 90.0%

Methyl 4-bromobutyrate (4897-84-1) + (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal (140647-02-5) → (2S)-N-[5'-methoxy-4'-[(3''-methoxycarbonylpropyl)oxy]-2'-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (349536-25-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

3-methoxy-4-hydroxybenzoic acid (121-34-6) → (2S)-N-[5'-methoxy-4'-[(3''-methoxycarbonylpropyl)oxy]-2'-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (349536-25-0)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃ / dimethylformamide / 2 h / 100 - 110 °C

2: 2.80 g / aq. NaOH / ethanol / 1 h / Heating

3: 62.2 percent / aq. HNO₃ / 1 h / 0 - 20 °C

4: 82.6 percent / p-TsOH / 4 h / 20 °C

5: (COCl)2; DMF / tetrahydrofuran / 4 h / 20 °C

6: 317 mg / Et₃N / CH₂Cl₂ / 2 h / cooling

With sodium hydroxide; oxalyl dichloride; nitric acid; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja005658r

Reference yield:

4-[(3'-carboxypropyl)oxy]-3-methoxybenzoic acid (349536-22-7) → (2S)-N-[5'-methoxy-4'-[(3''-methoxycarbonylpropyl)oxy]-2'-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (349536-25-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 62.2 percent / aq. HNO₃ / 1 h / 0 - 20 °C

2: 82.6 percent / p-TsOH / 4 h / 20 °C

3: (COCl)2; DMF / tetrahydrofuran / 4 h / 20 °C

4: 317 mg / Et₃N / CH₂Cl₂ / 2 h / cooling

With oxalyl dichloride; nitric acid; toluene-4-sulfonic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja005658r

upstream raw materials:

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

Methyl 4-bromobutyrate

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

(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl dithioacetal

Downstream raw materials:

4-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-N-chrysen-6-yl-butyramide

4-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-N-chrysen-6-yl-butyramide

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

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