L-Proline → HCID 15453762, compound

HRID 1108386Notes

Reaction equation

HRID 1108386 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[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].[NH2:27][C:28]1[C:33]([CH:34]=O)=[CH:32][CH:31]=[CH:30][N:29]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:34][C:33]3[C:28](=[N:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[C:8]1=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 15453761HCID 15453761, compound

Product 1

HCID 15453762HCID 15453762, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-7 (430 mg, 1.18 mmol), 2-amino-3-formylpyridine (144 mg, 1.18 mmol; for prep., see JOC 1983,48, 3401) and proline (136 mg, 1.18 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 2-8 as a yellow solid.

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-91e8f060dfd84c1e89ea8c02c39fbe6d
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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