1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine

Base Information

• Chemical Name: 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine
• CAS No.: 317861-00-0
• Molecular Formula: C₂₉H₃₂N₂O₇S
• Molecular Weight: 552.648
• Mol file: 317861-00-0.mol

Synonyms:1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine

Chemical Property of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine

There total 9 articles about 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine 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: 57.0%

(-)-(2S)-2-benzyloxy-3-phenylpropanoic acid (69127-81-7,97510-93-5) + 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-aminopyrrolidine (204072-63-9) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine (317861-00-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm000246e

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine (317861-00-0)

Guidance literature:

Multi-step reaction with 6 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: 57 percent / N-methylmorpholine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; hydroxybenzotriazole / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; dmap; formic acid; thionyl chloride; sodium azide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 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)-N-(1-oxy-2-benzyloxy-3-phenylpropyl)aminopyrrolidine (317861-00-0)

Guidance literature:

Multi-step reaction with 6 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: 57 percent / N-methylmorpholine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; hydroxybenzotriazole / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; dmap; formic acid; thionyl chloride; sodium azide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

upstream raw materials:

(-)-(2S)-2-benzyloxy-3-phenylpropanoic acid

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-aminopyrrolidine

L-3-phenyllactic acid

benzyl bromide