HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Proline → 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[3-(3-[1,8]naphthyridin-2-yl-propyl)-2-oxo-pyrrolidin-1-yl]-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | 3-Pyridinecarboxaldehyde, 2-amino- | HCID 737633 | — |
| Reactant | 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[2-oxo-3-(4-oxo-pentyl)-pyrrolidin-1-yl]-propionic acid ethyl ester | HCID 15453769 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[3-(3-[1,8]naphthyridin-2-yl-propyl)-2-oxo-pyrrolidin-1-yl]-propionic acid ethyl ester | HCID 15453770 | — |
Reaction Steps
A mixture of 4-2 (540 mg, 1.4 mmol), 2-amino-3-formylpyridine (170 mg, 1.4 mmol; for prep. see JOC 1983,48, 3401) and proline (161 mg, 1.4 mmol) in absolute ethanol (20 mL) was heated at reflux for 12 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 50% ethyl acetate/chloroform 70:25:5 chloroform/ethyl acetate/MeOH) to give 4-3 as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06268378B1 |
| Source dataset | uspto-grants-2001_07 |
| ORD ID | ord-12794d05f0ab4b31a855178657e2dea5 |
| Source note | uspto-grants-2001_07 |