L-Proline → HCID 54356438, compound

HRID 322517Notes

Reaction equation

HRID 322517 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C@H:10]([CH3:11])[CH2:9][C@H:8]([CH2:12][CH2:13][C:14](=O)[CH3:15])[C:7]1=[O:17])[CH3:2].[NH2:19][C:20]1[C:25]([CH:26]=O)=[CH:24][CH:23]=[CH:22][N:21]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C@H:10]([CH3:11])[CH2:9][C@H:8]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:26][C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[C:7]1=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 54116747HCID 54116747, compound

Product 1

HCID 54356438HCID 54356438, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11-9 (220 mg, 0.8619 mmol), 1-4, 2-amino-3-formylpyridine (137 mg, 1.12 mmol) and proline (99 mg, 0.8619 mmol) in absolute ethanol (5 mL) was heated at reflux for 12 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:25:5 chloroform/ethyl acetate/MeOH) to give 11-10 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, 70:25:5 chloroform/ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-baedbcd779ce4422a836bf4d67b1d7a4
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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