HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diazomethane → Diphenylmethyl (6R-trans)-3-methoxy-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diazomethane | HCID 9550 | — |
| Reactant | 3-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester | HCID 54708251 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | Diphenylmethyl (6R-trans)-3-methoxy-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate | HCID 6453042 | — |
Reaction Steps
The resulting crude 7β-phenoxyacetamido-3-hydroxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester is dissolved in methanol and a solution of diazomethane in ether is added at 0° C. After 10 minutes, the solution is carefully concentrated and the residue is dried under a high vacuum. The residue is purified by thick layer chromatography (toluene/ethyl acetate, 3:1, silica gel). After eluting the silica gel of the zone at Rf = 0.17 with ethyl acetate, and concentrating the solution on a rotary evaporator, 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester is obtained; melting point 120° C. (from ether).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04147864 |
| Source dataset | uspto-grants-1979_04 |
| ORD ID | ord-33ed86bd9a78465cbe69139ce8a64073 |
| Source note | uspto-grants-1979_04 |