HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ertapenem
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | HCID 10304013 | — |
| Reactant | 1-[(4-Nitrophenyl)methyl] (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylate | HCID 15409260 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ertapenem | HCID 150610 | — |
Reaction Steps
To 3-[[[(2S,4S)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid (7.68 g) in DMF (30 mL), p-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[(diphenylphosphono)oxy]-1-methylcarbapen-2em-3-carboxylate (10 g) was added. To the reaction mixture N,N-diisopropylethylamine (4.78 g) was added at −30° C. and stirred. After completion of reaction, the reaction mass was poured into water and ethyl acetate mixture at 10° C. The layers were separated and organic layer washed with brine solution. The organic layer was subjected to carbon treatment and taken for subsequent step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08293894B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-74a0627d0e6644a7bd9fc3bf79cda160 |
| Source note | uspto-grants-2012_10 |