HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 7-[2-Methoxyimino-3,3-dimethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Acetamide, 2-(trimethylsilyl)- | HCID 357676 | — |
| Reactant | (6R)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid | HCID 13072520 | — |
| Reactant | 2-Methoxyimino-3,3-dimethoxy-4-bromobutyric acid | HCID 53996198 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 7-[2-Methoxyimino-3,3-dimethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid | HCID 86738092 | 79.8% |
Reaction Steps
7-Amino-3-hydroxycepham-4-carboxylic acid (2.18 g, purity 84.8%), trimethylsilylacetamide (10.5 g.), 2-methoxyimino-3,3-dimethoxy-4-bromobutyric acid (syn isomer, 3.24 g.), N,N-dimethylformamide (1.1 ml), phosphorus oxychloride (1.36 ml) and methylene chloride (50 ml.) were treated in a similar manner to that of Example 25 (1) to give 7-[2-methoxyimino-3,3-dimethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 3.75 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04518774 |
| Source dataset | uspto-grants-1985_05 |
| ORD ID | ord-dd3cdc39536c461eba816c07c3f30945 |
| Source note | uspto-grants-1985_05 |