L-Proline → HCID 86756579, compound

HRID 322082Notes

Reaction equation

HRID 322082 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:9][CH2:10][C:11](=O)[CH3:12])[CH3:6])[CH3:2].[NH2:22][C:23]1[C:28]([CH:29]=O)=[CH:27][CH:26]=[CH:25][N:24]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:29][C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 86756578HCID 86756578, compound

Product 1

HCID 86756579HCID 86756579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-6 (12 g, 40 mmol), 2-amino-3-formylpyridine (6.3 g, 52 mmol), proline (4.6 g, 40 mmol) and ethanol (300 mL) was heated at reflux for 15 h. After cooling and evaporation, the residue was chromatographed (silica gel, 1:1 chloroform/ethyl acetate) to give 4-7 as a yellow oil.

Workup

  1. temperatureat reflux for 15 h
  2. temperatureAfter cooling
  3. customevaporation
  4. customthe residue was chromatographed (silica gel, 1:1 chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-342e9c10c45243bf9f573731b2761e82
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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