Salicylaldehyde → HCID 86749326, compound

HRID 1440033Notes

Reaction equation

HRID 1440033 reaction equation
N[C@H:2]([C:9]([OH:11])=[O:10])CC1N=CNC=1.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[CH:22](=[O:30])[C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[OH:25]>C(O)(=O)C>[C:9]([OH:11])(=[O:10])[CH3:2].[CH:22](=[O:30])[C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[OH:25]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 444305L-Tartaric acidHCID 178419078HCID 178419078, compound2×

Product 1

HCID 86749326HCID 86749326, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture consisting of 15.5 g L-histidine, 15.1 g L-(+)-tartaric acid was added 85 ml of the recovered acetic acid solution containing salicylaldehyde from the previous experiment. Additional 10 ml acetic acid containing 0.54 ml salicylaldehyde was added, and the mixture was stirred and heated as above at 80°-100° C. for two hours. After cooling to 25° C. the crude product D-His-(+)TA was filtered. 79 ml of acetic acid containing salicylaldehyde was recovered (83.2%). After stirring in hot water as above, pure D-His-(+)TA was obtained, 25.9 g (85% yield from L-His).

Workup

  1. temperatureheated as above at 80°-100° C. for two hours
  2. filtrationwas filtered
  3. addition79 ml of acetic acid containing salicylaldehyde
  4. customwas recovered (83.2%)
  5. stirringAfter stirring in hot water as above, pure D-His-(+)TA
  6. customwas obtained

Sources & evidence

ORD record
ord-a07d3a6713354e90950d1a9b0a66928e
Source dataset
uspto-grants-1996_03
Patent number
US05496955

Reaction notes

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