L-Proline → HCID 53827885, compound

HRID 379271Notes

Reaction equation

HRID 379271 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=O)[CH3:14])[CH3:2].N1CCC[C@H]1C(O)=O.[NH2:25][C:26]1[C:31]([CH:32]=O)=[CH:30][CH:29]=[CH:28][N:27]=1>CCO>[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:32][C:31]2[C:26](=[N:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1)[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 54440811HCID 54440811, compound

Product 1

HCID 53827885HCID 53827885, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 28-3 (4.1 g, 18.3 mmol), proline (2.7 g, 23.8 mmol), and 1-3 (2.9 g, 23.8 mmol ) in 50 mL EtOH was heated at 110° C. for 24 hr. The reaction mixture was concentrated and purified by silica gel chromatography (EtOAc, 100%) to afford the desired product 28-4 as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography (EtOAc, 100%)

Sources & evidence

ORD record
ord-e1559f699e364314a53ec9bf1cd3ced4
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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