HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 7-[[[2-[(Diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxyimino) acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)-methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4-methoxyphenyl)methyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | (2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetic acid | HCID 15028031 | — |
| Reactant | 3-(Chloromethyl)-7-[[[2-[(diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxy-imino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (4-methoxyphenyl)methyl ester | HCID 86745851 | — |
| Reactant | HCID 178527745 | HCID 178527745 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 7-[[[2-[(Diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxyimino) acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)-methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4-methoxyphenyl)methyl Ester | HCID 76508043 | 76.8% |
Reaction Steps
[6R-[6-α, 7-β (Z)]]-3-(chloromethyl)-7-[[[2-[(diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxy-imino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (4-methoxyphenyl)methyl ester (0.8 g) and 0.4 g sodium 5-mercapto-1,2,3-thiadiazole were stirred in 30 ml acetone plus 15 ml water for 30 minutes. The solvent was evaporated to dryness and the residue was columned on Biosil A using methylene chloride containing 0.5 to 1.0% methanol to give 687 mg of product; MS ((+)FAB) 770 (M+H); IR (KBr,cm-1) 1786, 1720.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05116827 |
| Source dataset | uspto-grants-1992_05 |
| ORD ID | ord-40e80d0a51004e75a3044e6c285b65d1 |
| Source note | uspto-grants-1992_05 |