HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Benzyloxy-alpha-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide → alpha-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-N-hydroxy-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Benzyloxy-alpha-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide | HCID 19705472 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Palladium hydroxide | HCID 9942167 | — |
| Product | alpha-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-N-hydroxy-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide | HCID 19705439 | 79.3% |
Reaction Steps
A mixture of N-benzyloxy-α-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (58 mg, 0.10 mmol) and 5% Pd/C (20 mg) is stirred for 1.5 hours at room temperature under an atmosphere of hydrogen. Palladium hydroxide on carbon (10 mg) is added and the mixture is stirred under hydrogen at room temperature for 6 hours. The mixture is filtered and the filtrate is concentrated. Purification by column chromatography (5% MeOH/EtOAc) gives 39 mg of an oil which is crystallized from EtOAc/hexane to give 29 mg (59%) of the title compound as a white solid (mp 158°-159° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05712300 |
| Source dataset | uspto-grants-1998_01 |
| ORD ID | ord-9af53fa0bb544fa49734199a6b8892bb |
| Source note | uspto-grants-1998_01 |