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| | 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 Structure](CAS/GIF/202467-69-4.gif) |
| | 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 Preparation Products And Raw materials |
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