4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester
• CAS No.: 912291-98-6
• Molecular Formula: C₃₄H₄₄N₄O₁₀
• Molecular Weight: 668.744
• Mol file: 912291-98-6.mol

Synonyms:4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester

Chemical Property of 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester

There total 10 articles about 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester 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: 27.0%

4-nitro-benzoic acid 1-(2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-(1-methoxycarbonyl-2-vinylcyclopropylcarbamoyl)-pyrrolidin-3-yl ester (912291-94-2) → (1S,4R,6S,7Z,14S,18S)-14-cyclopentyloxycarbonylamino-18-(4-nitro-benzoyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester (912291-95-3) + (1S,4R,6S,7Z,14S,18S)-14-cyclopentyloxycarbonylamino-18-(4-nitro-benzoyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester + 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester (912291-98-6)

Guidance literature:

With tricyclohexylphosphine; dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II); In toluene; at 60 ℃;

DOI:10.1021/jo060285j

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester (912291-98-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / EDC; i-Pr₂NEt / dimethylformamide / 24 h / 20 °C

2: 70 percent / PPh₃; DEAD / tetrahydrofuran / cooling

3: HCl / dioxane / 3 h / 20 °C

4: 0.98 g / i-Pr₂NEt; TBTU / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo061587o

Reference yield:

4-nitro-benzoic acid (62-23-7) → 4-Nitro-benzoic acid (3S,5S)-1-((S)-2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester (912291-98-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / PPh₃; DEAD / tetrahydrofuran / cooling

2: HCl / dioxane / 3 h / 20 °C

3: 0.98 g / i-Pr₂NEt; TBTU / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jo061587o

upstream raw materials:

4-nitro-benzoic acid 1-(2-cyclopentyloxycarbonylamino-non-8-enoyl)-5-(1-methoxycarbonyl-2-vinylcyclopropylcarbamoyl)-pyrrolidin-3-yl ester

(S)-2-cyclopentyloxycarbonyl-amino-8-nonenoic acid

(2S,4R)-4-Hydroxy-2-((1R,2R)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid