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

HRID 1108394Notes

Reaction equation

HRID 1108394 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C@@H:6]([C:19]1[CH:27]=[CH:26][C:22]2[CH2:23][CH2:24][O:25][C:21]=2[CH:20]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15](=O)[CH3:16])[C:8]1=[O:18])[CH3:2].[NH2:29][C:30]1[C:35]([CH:36]=O)=[CH:34][CH:33]=[CH:32][N:31]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C@@H:6]([C:19]1[CH:27]=[CH:26][C:22]2[CH2:23][CH2:24][O:25][C:21]=2[CH:20]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:36][C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)[C:8]1=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 154537693(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[2-oxo-3-(4-oxo-pentyl)-pyrrolidin-1-yl]-propionic acid ethyl ester

Product 1

HCID 154537703(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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 50% ethyl acetate/chloroform 70:25:5 chloroform/ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-2fc412fa27eb4e2184a39ecd42c04c88
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

Loading…