L-Proline → HCID 20691579, compound

HRID 1837931Notes

Reaction equation

HRID 1837931 reaction equation
O=[C:2]([CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[NH2:14][C:15]1[C:20]([CH:21]=O)=[CH:19][CH:18]=[CH:17][N:16]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH3:12][O:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1[CH:13]=[CH:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 538606Methyl 8-oxononanoateHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 20691579HCID 20691579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of methyl 8-oxo-nonanoate 29-2 (3.8 g, 20.4 mmol) in absolute ethanol (100 mL) was added 2-aminopyridine-3-carboxaldehyde (2.49 g, 20.4 mmol) and L-proline (1.17 g, 10.2 mmol) and the mixture was heated to 95° C. for 18 hours, after which the mixture was cooled to ambient temperature and then concentrated at reduced pressure. The resulting solid was purified by flash column chromatography over silica gel with 95:5 ethyl acetate/methanol to give 29-3 as a white solid.

Workup

  1. temperatureafter which the mixture was cooled to ambient temperature
  2. concentrationconcentrated at reduced pressure
  3. customThe resulting solid was purified by flash column chromatography over silica gel with 95:5 ethyl acetate/methanol

Sources & evidence

ORD record
ord-d60c05e0a5af41f49c139db38375929a
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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