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 1387437Notes

Reaction equation

HRID 1387437 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-12794d05f0ab4b31a855178657e2dea5
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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