3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid

Base Information

• Chemical Name: 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid
• CAS No.: 1301189-87-6
• Molecular Formula: C₁₇H₂₃N₃O₆
• Molecular Weight: 365.386
• Mol file: 1301189-87-6.mol

Synonyms:3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid

Chemical Property of 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid

There total 5 articles about 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid 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:

3-fluoro-4-nitrobenzoic acid (403-21-4) + tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate (270912-72-6) → 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid (1301189-87-6)

Guidance literature:

In dimethyl sulfoxide; at 98 ℃; for 17h; Inert atmosphere;

Reference yield:

C-(1-benzyl-pyrrolidin-3-yl)-methylamine (93138-61-5) → 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid (1301189-87-6)

Guidance literature:

Multi-step reaction with 5 steps

1: dichloromethane / 12 h / 0 - 20 °C

2: hydrogen / palladium(II) hydroxide; palladium 10% on activated carbon / acetic acid; methanol / 48 h / 20 °C

3: triethylamine / methanol / 24 h / 0 - 20 °C

4: sodium hydroxide; water / methanol / 3 h / 20 °C

5: dimethyl sulfoxide / 17 h / 98 °C / Inert atmosphere

With water; hydrogen; triethylamine; sodium hydroxide; palladium 10% on activated carbon; palladium(II) hydroxide; In methanol; dichloromethane; acetic acid; dimethyl sulfoxide;

Reference yield:

2,2,2-trifluoro-N-{[(3RS)-1-(phenylmethyl)-3-pyrrolidinyl]methyl}acetamide (849632-74-2) → 3-{[((3RS)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]amino}-4-nitrobenzoic acid (1301189-87-6)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / palladium(II) hydroxide; palladium 10% on activated carbon / acetic acid; methanol / 48 h / 20 °C

2: triethylamine / methanol / 24 h / 0 - 20 °C

3: sodium hydroxide; water / methanol / 3 h / 20 °C

4: dimethyl sulfoxide / 17 h / 98 °C / Inert atmosphere

With water; hydrogen; triethylamine; sodium hydroxide; palladium 10% on activated carbon; palladium(II) hydroxide; In methanol; acetic acid; dimethyl sulfoxide;

upstream raw materials:

3-fluoro-4-nitrobenzoic acid

tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate

C-(1-benzyl-pyrrolidin-3-yl)-methylamine

1,1-dimethylethyl (3RS)-3-{[(trifluoroacetyl)amino]methyl}-1-pyrrolidinecarboxylate

Downstream raw materials:

2-(4-biphenylyl)-1-[((3R₅)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)methyl]-1H-benzimidazole-6-carboxylic acid

1,1-dimethylethyl (3RS)-3-({2-(4-biphenylyl)-6-[(methylamino)carbonyl]-1H-benzimidazol-1-yl}methyl)-1-pyrrolidinecarboxylate

2-(4-biphenylyl)-N-methyl-1-[(3RS)-3-pyrrolidinylmethyl]-1H-benzimidazole-6-carboxamide

2-(4-biphenylyl)-1-({(3RS)-1-[(dimethylamino)carbonyl]-3-pyrrolidinyl}methyl)-N-methyl-1H-benzimidazole-6-carboxamide