Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 70545261 | HCID 70545261 | — |
| Solvent | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Product | HCID 70542895 | HCID 70542895 | 159.2% |
Reaction Steps
A solution of 34 mmoles of p-nitrobenzyl 6-amino-2,2-dimethylpenam-3-carboxylate (6APA p-nitrobenzyl ester) in 100 ml of dimethylformamide dimethylacetal was stirred at room temperature for three hours. The reaction mixture was then poured into a stirred mixture of ice water and ethyl acetate and the organic phase separated. The organic phase was layered over water and the pH adjusted to 1.8 with hydrochloric acid. The acidified aqueous layer was separated, slurried with ethyl acetate, and the pH adjusted to 7.5 with 1 N sodium hydroxide. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated to dryness. The product was obtained as a residual oil and was crystallized in trituration with diethyl ether. There were obtained 11 g (80% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04316842 |
|---|
| Source dataset | uspto-grants-1982_02 |
|---|
| ORD ID | ord-be4f19f1962448b4a9c8c2bad87ca9e3 |
|---|
| Source note | uspto-grants-1982_02 |
|---|