| Identification | More | [Name]
3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid | [CAS]
202467-69-4 | [Synonyms]
2-[[(3-Carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylic acid (2S-cis)-1-[(4-nitrophenyl)methyl] ester
3-[[[(2s,4s)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid
3-[[[(2S,4S)-4-MERCAPTO-2-PYRROLIDINYL-1-(4-NITROBENZYLOXY)CARBONYL]CARBONYL]AMINO]BENZOIC ACID
(2S, 4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidinecarboxylate
SIDE CHAIN FOR ERTAPENEM
ERTAPENEM SIDE CHAIN 1
2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylic acid (2s-cis)-1-[(4-nitrophenyl)methyl] ester
4-NITROBENZYL-(2S, 4S)-2-[[(3-CARBOXYPHENYL)AMINO]CARBONYL]-4-MERCAPTO-1-PYRROLIDINECARBOXYLATE
ERTAPENEM SIDE CHAIN, 3-[[[(2S,4S)-4-MERCAPTO-1-(4-NITROBENZYLOXY)CARBONYL-2-PYRROLIDINYL]CARBONYL]AMINO]BENZOIC ACID
3-[[[(2S, 4S)-4-MERCAPTO-1-TERT-BUTOXYCARBONYL-2-PYRROLIDINYL]CARBONYL]AMINO]BENZOIC ACID
SIDECHAINIFORERTAPENEM | [EINECS(EC#)]
606-474-0 | [Molecular Formula]
C20H19N3O7S | [MDL Number]
MFCD09263754 | [Molecular Weight]
445.45 | [MOL File]
202467-69-4.mol |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
4.06±0.10(Predicted) | [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) |
| Hazard Information | Back Directory | [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 |
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