HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one → 5-{2-Hydroxy-4-[2-(2H-pyrazol-3-yl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one | HCID 68917001 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-{2-Hydroxy-4-[2-(2H-pyrazol-3-yl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one | HCID 24970184 | — |
Reaction Steps
5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one (240 mg, 0.40 mmol) is dissolved in methanol (5 mL). 10% Pd/C is added periodically (7×50 mg) at intervals over 4 days. The mixture is stirred under an atmosphere of hydrogen at balloon pressure. The catalyst is removed by filtering the mixture through Celite and the filtrate is concentrated. The residue is chromatographed (reverse phase, 0-25% EtOH/water) to afford the title compound as a grey solid: 1H NMR (CD3OD) δ 7.46 (s, 1H), 7.31 (d, J=8.0 Hz, 1H), 6.75 (s, 1H), 6.71 (d, J=8.0 Hz, 1H) 6.10 (s, 1H) 4.29 (s, 2H), 2.89 (m, 4H); (M+1)+=323.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084448B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-25b3ef4150e543e39003306c5dffa8b1 |
| Source note | uspto-grants-2011_12 |