HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Bromoethyl acetate → 1-acetyloxyethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-3-methoxyprop-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Bromoethyl acetate | HCID 11137505 | — |
| Reactant | (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-3-methoxyprop-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | HCID 88669300 | — |
| Product | 1-acetyloxyethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-3-methoxyprop-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | HCID 88668980 | 43% |
Reaction Steps
Esterification of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-3-methoxy-1-propenyl]-3-cephem-4-carboxylic acid (300 mg, 0.66 mmole) with 1-bromoethyl acetate in a similar manner to that described in Example 10 gave the title compound (154 mg, 43%). Mp. 102°-105° C. (dec.). Estimated purity 95% (by HPLC, 1:1 CH3CN-pH 7 phosphate buffer).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04708955 |
| Source dataset | uspto-grants-1987_11 |
| ORD ID | ord-23ab77e49c2e47e6a0ad73755e4e3694 |
| Source note | uspto-grants-1987_11 |