L-Proline → HCID 70234942, compound

HRID 1387441Notes

Reaction equation

HRID 1387441 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14]C(=O)C)[C:8]1=[O:18])[CH3:2].[NH2:30][C:31]1[C:36]([CH:37]=O)=[CH:35][CH:34]=[CH:33][N:32]=1.N1CCC[C@H:40]1[C:41](O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:33]2[CH:34]=[CH:35][C:36]3[C:31](=[N:30][CH:40]=[CH:41][CH:37]=3)[N:32]=2)[C:8]1=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 68819508HCID 68819508, compound

Product 1

HCID 70234942HCID 70234942, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-2 (396 mg, 1.0 mmol), 2-amino-3-formylpyridine (138 mg, 1.2 mmol; for prep. see JOC 1983,48, 3401) and proline (218 mg, 2.0 mmol) in absolute ethanol (15 mL) was heated at reflux for 12 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 50% ethyl acetate/chloroform to 70:25:5 chloroform/ethyl acetate/MeOH) to give 6-3 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, 50% ethyl acetate/chloroform to 70:25:5 chloroform/ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-9665b6238c3644aba2cd50c53cddb256
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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