1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine

Base Information

• Chemical Name: 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine
• CAS No.: 317860-09-6
• Molecular Formula: C₁₆H₂₂N₂O₇S₂
• Molecular Weight: 418.492

Synonyms:1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine

Chemical Property of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine

Chemical Property:

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Technology Process of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine

There total 8 articles about 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine 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: 77.0%

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-chlorosulfonamido)pyrrolidine (317860-07-4) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine (317860-09-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/jm000246e

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine (317860-09-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N; DMAP / H₂O; dioxane / 14 h / 20 °C

2: SOCl₂ / 14 h

3: Et₃N / CH₂Cl₂ / 20 °C

4: 79 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

5: 58 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

6: 67 percent / Et₃N / CH₂Cl₂ / 18 h

7: 77 percent / DBU / dimethylformamide / 18 h

With dmap; formic acid; thionyl chloride; sodium azide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-sultam-1N-yl)pyrrolidine (317860-09-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N; DMAP / H₂O; dioxane / 14 h / 20 °C

2: SOCl₂ / 14 h

3: Et₃N / CH₂Cl₂ / 20 °C

4: 79 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

5: 58 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

6: 67 percent / Et₃N / CH₂Cl₂ / 18 h

7: 77 percent / DBU / dimethylformamide / 18 h

With dmap; formic acid; thionyl chloride; sodium azide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

upstream raw materials:

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(γ-chlorosulfonamido)pyrrolidine

4-methoxy-phenyl-sulphonyl chloride

cis-hydroxy-D-proline

(2R,4R)-4-Hydroxy-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

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