L-Proline → HCID 20691580, compound

HRID 1004262Notes

Reaction equation

HRID 1004262 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=O)[CH3:13].[NH2:16][C:17]1[C:22]([CH:23]=O)=[CH:21][CH:20]=[CH:19][N:18]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:23][C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 519622Methyl 10-oxoundecanoateHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 20691580HCID 20691580, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13-2 (9.2 g, 43 mmol), 1-3 (5.3 g, 43 mmol), proline (2.5 g, 22 mmol), and ethanol (215 mL) was heated to reflux for 20 h. The cooled reaction mixture was concentrated and the residue purified by flash chromatography (silica, EtOAc) to give 13-3 as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. customthe residue purified by flash chromatography (silica, EtOAc)

Sources & evidence

ORD record
ord-6f64c92b52ac401daa7abc149d150628
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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