Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 15582369 | HCID 15582369 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 15582366 | HCID 15582366 | 69.5% |
Reaction Steps
To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-[2-(1H-tetrazol-1-yl)acetamido]penam-3-carboxylate (0.91 g.) in a mixture of dimethylformamide (5 ml.) and acetic acid (1.5 ml.) was added zinc powder (1.2 g.) under ice-cooling, and the mixture was stirred for 1 hour. After the reaction, the reaction mixture was poured into a mixture of 2% hydrochloric acid saturated with sodium chloride (30 ml.) and ethyl acetate (50 ml.), extracted and the aqueous layer was further extracted with ethyl acetate (10 ml.). The combined ethyl acetate layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After drying, residue obtained by distilling off the solvent under reduced pressure was crystallized by adding a small amount of ethyl acetate and the crystals were collected by filtration to give 2-methyl-2,3-methylene-6-[2-(1H-tetrazol-1-yl)acetamido]penam-3-carboxylic acid (0.45 g.), mp 167° to 170°C (dec.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US03984397 |
|---|
| Source dataset | uspto-grants-1976_10 |
|---|
| ORD ID | ord-e739e6057b4d494dbb757b1a882a437b |
|---|
| Source note | uspto-grants-1976_10 |
|---|