L-Proline → HCID 54356438, compound

HRID 1602637Notes

Reaction equation

HRID 1602637 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-c72f97bf7b0e4a9ca9cd8f7bbc5fb1aa
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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