1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine

Base Information

• Chemical Name: 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine
• CAS No.: 317861-01-1
• Molecular Formula: C₂₆H₃₄N₂O₇S
• Molecular Weight: 518.631

Synonyms:1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine

Chemical Property of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine

Chemical Property:

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Technology Process of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine

There total 9 articles about 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine 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: 44.0%

(S)-2-(benzyloxy)propanoic acid (33106-32-0) + 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-propylaminopyrrolidine (204072-67-3) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine (317861-01-1)

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-benzyloxypropyl)-N-propylaminopyrrolidine (317861-01-1)

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: NaCNBH₃; AcONa; AcOH / methanol / 48 °C

7: 44 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; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; methanol; 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-benzyloxypropyl)-N-propylaminopyrrolidine (317861-01-1)

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: NaCNBH₃; AcONa; AcOH / methanol / 48 °C

7: 44 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; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

upstream raw materials:

(S)-2-(benzyloxy)propanoic acid

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

benzyl bromide

4-methoxy-phenyl-sulphonyl chloride

Downstream raw materials:

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine

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