L-Proline → HCID 20691579, compound

HRID 1004294Notes

Reaction equation

HRID 1004294 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-c06b883265c141888e5e3caa1586a223
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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