3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid CAS
Introduction：Basic information about 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid CAS, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid Basic information
| Product Name: | 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid |
| Synonyms: | 3-([[(2S,4S)-4-Mercapto-1-((4-nitrobenzyloxy)carbonyl)pyrrolidin-2-yl]carbonyl]aMino)benzoic acid;The Sidechain of Ertapenem;2-[(3-carboxyanilino)-oxomethyl]-4-mercapto-4-nitro-2-(phenylmethyl)-1-pyrrolidinecarboxylate;Ertaipenem side chain;Ertapenem side chain, Side chain for Ertapenem;Ertapenem side chains;[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid;Side Train of Ertapenem |
| CAS: | 202467-69-4 |
| MF: | C20H19N3O7S |
| MW: | 445.45 |
| EINECS: | 606-474-0 |
| Product Categories: | |
| Mol File: | 202467-69-4.mol |
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) |
Safety Information
| 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 | 99-05-8 151072-00-3 202467-69-4 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 Preparation Products And Raw materials
| Raw materials | 2-Thia-5-azabicyclo[2.2.1]heptane-5-carboxylic acid, 3-oxo-, (4-nitrophenyl)methyl ester, (1S,4S)--->TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE-->4-Nitrobenzyl chloroformate-->3-Aminobenzoic acid-->L-Hydroxyproline-->Hydrochloric acid-->Methanol-->Tributylphosphine |
