Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | HCID 20281146 | HCID 20281146 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 20281155 | HCID 20281155 | 83.2% |
Reaction Steps
2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (10.1 g) is added to a solution of p-toluenesulphonic acid monohydrate (8.15 g) in acetonitrile (170 cc), warmed to 35° C., and the mixture is left at 35° C. for 1 hour, whilst stirring. The reaction mixture is then poured into a stirred mixture of a saturated solution of sodium bicarbonate (150 cc) and ethyl acetate (300 cc). The organic phase is then washed with distilled water (100 cc), dried over magnesium sulphate and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields crude 7-amino-2-benzhydryloxycarbonyl-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (7 g) in the form of a thick oil which can be used without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04520193 |
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| Source dataset | uspto-grants-1985_05 |
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| ORD ID | ord-5745a487c5fb4423b76afc338a56a022 |
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| Source note | uspto-grants-1985_05 |
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