L-Alanine → HCID 178462050, compound

HRID 2392817Notes

Reaction equation

HRID 2392817 reaction equation
[OH-].[Na+:2].[NH2:3][C@H:4]([C:6]([OH:8])=O)[CH3:5].[C-:9]1([CH:14]=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10]1.[CH-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[Fe+2:21].[NH2:22][C@H](C([O-])=O)C>CCCCC.C(O)C>[NH2:3][C@H:4]([C:6](=[NH:22])[O-:8])[CH3:5].[Na+:2].[C-:9]1([CH:14]=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10]1.[CH-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[Fe+2:21]

Participants

7

Reactant 4

HCID 5950L-AlanineHCID 14798Sodium HydroxideHCID 5460980HCID 5460980, compoundHCID 15184314Ferrocenecarboxyaldehyde

Product 1

HCID 178462050HCID 178462050, compoundYield 950%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8003PentaneSolvent

Procedure

Aqueous sodium hydroxide (11.2 mmol in 11 ml of water) was added to L-alanine (1.0 g, 11.22 mmol) and stirred for several minutes at room temperature. The solvent was removed in vacuo and the residue dried at 60° C. under high vacuum overnight. 4 Å molecular sieves, ferrocenecarboxaldehyde (11.78 mmol, 2.52 g) and absolute ethanol (50 ml) were added to the alaninate and stirred for 5 hours; the course of the reaction can be followed by IR. The molecular sieves were separated by filtration, the filtrate concentrated on a vacuum line and a red solid was obtained. Pentane (50 ml) was added and the mixture was stirred until a suspension was formed. This was filtered through a sinter and the residue was washed with pentane and dried under vacuum to give the title compound as a yellow-orange solid (3.28 g, 950%); νmax (KBr disc) 1641 s (C=N) and 1591 (CO2-) cm-1. The imine rapidly undergoes hydrolysis on silica or in the presence of water.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue dried at 60° C. under high vacuum overnight
  3. stirringstirred for 5 hours
  4. customthe course of the reaction
  5. customThe molecular sieves were separated by filtration
  6. concentrationthe filtrate concentrated on a vacuum line
  7. customa red solid was obtained
  8. stirringthe mixture was stirred until a suspension
  9. customwas formed
  10. filtrationThis was filtered through a sinter
  11. washthe residue was washed with pentane
  12. customdried under vacuum

Sources & evidence

ORD record
ord-c91ca3a37cd640a5ae772446192863a9
Source dataset
uspto-grants-1998_09
Patent number
US05801248

Reaction notes

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