HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 7-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| 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-diethoxy-4-bromobutyric acid | HCID 54323732 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 7-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid | HCID 86738093 | 68.7% |
Reaction Steps
7-Amino-3-hydroxycepham-4-carboxylic acid (10.9 g, purity 84.8%), 2-methoxyimino-3,3-diethoxy-4-bromobutyric acid (syn isomer, 17.9 g), phosphorus oxychloride (6.8 ml), N,N-dimethylformamide (5.5 ml), water (100 ml), acetone (50 ml.) and tetrahydrofuran (44 ml) were treated in a similar manner to that of Example 25 (1) to give 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 17.1 g.). The I.R. spectrum and N.M.R. spectrum of the compound were the same as those of Example 28.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04518774 |
| Source dataset | uspto-grants-1985_05 |
| ORD ID | ord-c38dab1213684758ac39ea94fb45400c |
| Source note | uspto-grants-1985_05 |