Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | tert-Butyl 3-[(acetyloxy)methyl]-7-chloro-5,5,8-trioxo-5lambda~6~-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | HCID 125700 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 67657566 | HCID 67657566 | 81.6% |
Reaction Steps
A mixture of t-butyl 7α-chloro-3-acetoxymethyl-3-cephem-4-carboxylate-1,1-dioxide (1.9 g), methylene chloride (3 ml), dimethylamine hydrochloride (0.817 g), t-butanol (80 ml) and formaldehyde solution (I.10 ml, 37% w/v in water) was heated to reflux at 90° C. for 3 hours. Solvent was removed under reduced pressure and the residue was dissolved in methylene chloride, washed with water, brine, dried and concentrated to give 1.6 g (81.6%) of t-butyl 7α-chloro-2-methylene-3-acetoxymethyl-3-cephem-4-carboxylate-1,1-dioxide, m.p. 148°-149° C. This product without further purification was used in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05264430 |
|---|
| Source dataset | uspto-grants-1993_11 |
|---|
| ORD ID | ord-6d88c87393c74a90a97ba49a5fa29a96 |
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| Source note | uspto-grants-1993_11 |
|---|
