3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid Chemical Properties

Boiling point:

749.6±60.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Methanol (Sparingly)

pka

4.06±0.10(Predicted)

form 

Solid

color 

Off-White

InChIKey

RTQKWWOSWDCUMA-IRXDYDNUSA-N

SMILES

N1(C(OCC2=CC=C([N+]([O-])=O)C=C2)=O)C[C@@H](S)C[C@H]1C(NC1=CC=CC(C(O)=O)=C1)=O

CAS DataBase Reference

202467-69-4(CAS DataBase Reference)

3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid Usage And Synthesis

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.

Synthesis

At 60 °C, m-aminobenzoic acid (9.45 g, 68.9 mmol) was dissolved in 200 g of methanol and 1 g of tributylphosphine and 400 ml of a methanolic solution of 4M HCl were added. Subsequently, 220 g of methanol solution of 4-nitrobenzyl (1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptane-5-carboxylate (19.8 g, 64.28 mmol) was slowly added. The reaction was stirred at the same temperature for 3 hours. After completion of the reaction, the slurry was cooled and filtered to obtain white crystals. The white crystals were washed with methanol and then dried under vacuum to afford 3-((2S,4S)-4-mercapto-1-(((4-nitrobenzyloxy)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid (127.8 g) in 97% molar yield and 99.2% HPLC purity.

References

[1] Patent: CN105566193, 2016, A. Location in patent: Paragraph 0014; 0015
[2] Patent: CN104130262, 2017, B. Location in patent: Paragraph 0132; 0133; 0134

3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid (202467-69-4)Related Product Information

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• CARBONYL SULFIDE
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• Glycine
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• Ertapenem
• PYRAZOPHOS
• BIAPENEM SIDE CHAIN
• Ertapenem impurity 3
• (4R,5S,6S)-3-[[(3S,5S)-1-[3-[[[(2S,4S)-4-[[(4R,5S,6S)-2-Carboxy-6-[(1R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-2-pyrrolidinyl]carbonyl]aMino]benzoyl]-5-[[(3-carboxyphenyl)aMino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid
• Ertapenem sodium
• 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride
• ErtapeneM IMpurity DIPP
• ErtapeneM Side Chain EnantioMer 1
• Ertapenem-d4 Disodium
• Malathion
• 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid