L-Proline → HCID 20691580, compound

HRID 1837900Notes

Reaction equation

HRID 1837900 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-8274830221474f10b903c2e6cafcade0
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

Loading…