L-Proline → HCID 69711854, compound

HRID 322074Notes

Reaction equation

HRID 322074 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C@@H:6]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][CH2:14][CH2:15][C:16](=O)[CH3:17])[C:8]1=[O:19])[CH3:2].[NH2:28][C:29]1[C:34]([CH:35]=O)=[CH:33][CH:32]=[CH:31][N:30]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C@@H:6]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:35][C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)[C:8]1=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 69710318HCID 69710318, compound

Product 1

HCID 69711854HCID 69711854, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-7 (450 mg, 1.2 mmol), 2-amino-3-formylpyridine (145 mg, 1.2 mmol; for prep., see JOC 1983,48, 3401) and proline (137 mg, 1.2 mmol) in absolute ethanol (20 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 2-8 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-687c72be89674a79964a4dd26aaa18e0
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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