L-Proline → HCID 53682092, compound

HRID 1602644Notes

Reaction equation

HRID 1602644 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C@H:8]([CH2:18][CH2:19][C:20](=O)[CH3:21])[C:7]1=[O:23])[CH3:2].[NH2:25][C:26]1[C:31]([CH:32]=O)=[CH:30][CH:29]=[CH:28][N:27]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C@H:8]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:32][C:31]3[C:26](=[N:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)[C:7]1=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 53984281HCID 53984281, compound

Product 1

HCID 53682092HCID 53682092, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12-5 (230 mg, 0.6940 mmol), 1-4, (2-amino-3-formylpyridine, 110 mg, 0.9022 mmol) and proline (80 mg, 0.6940 mmol) in absolute ethanol (10 mL) was heated at reflux for 18 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:28:2 chloroform/ethyl acetate/MeOH) to give 12-6 as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 70:28:2 chloroform/ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-760042c459f043368f01c09dac9e9330
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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