3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid

Base Information

• Chemical Name: 3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid
• CAS No.: 202467-69-4
• Molecular Formula: C20H19N3O7S
• Molecular Weight: 445.453
• Hs Code.: 2933990090
• European Community (EC) Number: 606-474-0
• UNII: 33DAX2G5P2
• DSSTox Substance ID: DTXSID201110222
• Nikkaji Number: J2.766.475J
• Mol file: 202467-69-4.mol

Synonyms:202467-69-4;3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid;3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid;3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)-carbonyl)pyrrolidine-2-carboxamido)benzoic acid;1-Pyrrolidinecarboxylic acid, 2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-, 1-[(4-nitrophenyl)methyl] ester, (2S,4S)-;3-[[(2S,4S)-1-[(4-nitrophenyl)methoxycarbonyl]-4-sulfanylpyrrolidine-2-carbonyl]amino]benzoic acid;1-[(4-Nitrophenyl)methyl] (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylate;C20H19N3O7S;3-((((2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl)carbonyl)amino)benzoic acid;3-[[[(2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-4-mercaptopyrrolidin-2-yl]carbonyl]amino]benzoic Acid;33DAX2G5P2;SCHEMBL4211429;DTXSID201110222;AMY41240;AKOS015889901;DS-17903;C73827;A814358;Q-101435;3-((2S,4S)-4-mercapto-1-((4-nitrobenzyloxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid;1-Pyrrolidinecarboxylic acid, 2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-, 1-[(4-nitrophenyl)methyl] ester, (2S-cis)-;3-(((2s,4s)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidine)carbonylamino)benzoic acid;3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoicacid;3-[[[(2S, 4S)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino];3-[[[(2S, 4S)-4-MERCAPTO-1-TERT-BUTOXYCARBONYL-2-PYRROLIDINYL]CARBONYL]AMINO]BENZOIC ACID;3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoicacid;3-[[[(2S,4S)-4-Mercapto-2-pyrrolidinyl-1-(4-nitrobenzyloxy)carbonyl]carbonyl]amino]benzoic acid

Chemical Property of 3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid

Chemical Property:

• Vapor Pressure: 1.33E-23mmHg at 25°C
• Refractive Index: 1.675
• Boiling Point: 749.6 °C at 760 mmHg
• PKA: 4.06±0.10(Predicted)
• Flash Point: 407.1 °C
• PSA: 180.56000
• Density: 1.5g/cm³
• LogP: 3.47510
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 445.09437113
• Heavy Atom Count: 31
• Complexity: 693

Purity/Quality:

99% ^*data from raw suppliers

3-[[[(2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-4-mercaptopyrrolidin-2-yl]carbonyl]amino]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)NC2=CC=CC(=C2)C(=O)O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])S
• Isomeric SMILES: C1[C@@H](CN([C@@H]1C(=O)NC2=CC=CC(=C2)C(=O)O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])S
• Uses: 3-[[[(2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-4-mercaptopyrrolidin-2-yl]carbonyl]amino]benzoic Acid is an intermediate in the preparation of Ertapenem (E635000) and intermediates.

Technology Process of 3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid

There total 8 articles about 3-((2S,4S)-4-Mercapto-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic 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: 97.0%

meta-aminobenzoic acid (99-05-8,159139-79-4) + (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one (151072-00-3) → (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidine carboxylate (202467-69-4)

Guidance literature:

With hydrogenchloride; tributylphosphine; In methanol; at 60 ℃; for 3h; Temperature; Solvent;

Reference yield:

C14H16N2O8S2 → (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidine carboxylate (202467-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water

2: acetic acid / 20 °C / Inert atmosphere

With hydrogenchloride; acetic acid; In water;

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidine carboxylate (202467-69-4)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydroxide / water; dichloromethane / 5 h / 0 - 5 °C / Large scale

2: triethylamine / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

3: triethylamine / 0.5 h / -15 °C

4: sodium sulfide; triethylamine / 1 h / 5 - 10 °C

5: hydrogenchloride / water

6: acetic acid / 20 °C / Inert atmosphere

With hydrogenchloride; sodium sulfide; acetic acid; triethylamine; sodium hydroxide; In dichloromethane; water;

upstream raw materials:

meta-aminobenzoic acid

(2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one

4R-4-hydroxyproline

(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

(2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride

(4-nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(-carboxyphenyl)amino]carbonyl]-1-[[(4-nitrophenyl)methyoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

3-((2S,4S)-1-((4-nitrobenzyloxy)carbonyl)-4-(tritylthio)pyrrolidine-2-carboxamido)benzoic acid

6-[5-(3-carboxy-phenylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-3,5-dimethyl-1-oxo-3,4,4a,5-tetrahydro-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid

Refernces

• 1、 -. "Improved manufacturing method of ertapenem side chain". Paragraph 0014; 0015. . Retrieved 2016/12/01.