HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diketene → 4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diketene | HCID 12661 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | Acetamide, 2-(trimethylsilyl)- | HCID 357676 | — |
| Reactant | Thiourea | HCID 2723790 | — |
| Reactant | Bistrimethylsilylacetamid | HCID 11708267 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | 4-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride | HCID 70362150 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate | HCID 131712505 | — |
Reaction Steps
A solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (15.0 g.), bis(trimethylsilyl)acetamide (11.3 g.) and trimethylsilylacetamide (9.7 g.) in tetrahydrofuran (300 ml.), a solution of diketene (3.41 ml.) in methylene chloride (4 ml.), a solution of bromine (2.27 ml.) in methylene chloride (4 ml.), a solution of sodium nitrite (3.1 g.) in water (20 ml.) and a solution of thiourea (4.0 g.) in water (40 ml.) were treated in a similar manner to that of Example 37-(1) to give 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 10.4 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04400379 |
| Source dataset | uspto-grants-1983_08 |
| ORD ID | ord-5f1cd10adda94c6f954f2a7abaaeb73e |
| Source note | uspto-grants-1983_08 |