HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Bromide → Clavulanic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Bromide | HCID 253877 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate) | HCID 9904055 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | Clavulanic Acid | HCID 5280980 | — |
Reaction Steps
Benzyl clavulanate (840 mgs) in ethanol (30 ml) and water (5 ml) was hydrogenated over 10% Pd/C (267 mgs) and sodium bicarbonate (244 mgs) for 25 minutes at room temperature and atmospheric pressure. The catalyst was filtered, washed with water and ethanol and the combined filtrates were evaporated in vacuo. The product crystallised from a water-acetone mixture as microneedles (565 mgs). Recrystallisation from water-acetone gave needles which, after drying over P2O5 in vacuo for 24 hours gave the following analysis: C 41.01, 40.86; H 3.77, 3.64; N 5.68, 5.51; i.r. (KBr disc) 1785, 1700, 1620 cm-1 ; Nmr (D2O) 3.06 (d,1,J=18.5Hz), 3.57 (dd,1,J1 =18.5Hz, J2 =2.5Hz), 4.15 (d,2,J=8Hz), 5.3 (HOD), 4.9 (m), 5.71 (d,1,J=2.5Hz)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04110165 |
| Source dataset | uspto-grants-1978_08 |
| ORD ID | ord-71d0e3f1e1ad4b6dbd90fb8bf4983b11 |
| Source note | uspto-grants-1978_08 |