p-Toluenesulfonic acid → HCID 178491127, compound

HRID 385763Notes

Reaction equation

HRID 385763 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:11][C@@H:12]([CH3:15])[CH2:13][OH:14].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[N:11]/[C@@H:12]([CH3:15])[CH2:13][OH:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 312444-MethoxybenzaldehydeHCID 80307L-Alaninol

Product 1

HCID 178491127HCID 178491127, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 10000 mL 4-necked, round bottomed flask purged and maintained with an inert atmosphere of nitrogen was placed 4-methoxybenzaldehyde (500 g, 3.67 mol), (S)-2-aminopropan-1-ol (276 g, 3.68 mol), 4-methylbenzenesulfonic acid (31.7 g, 184.09 mmol) and toluene (5000 mL). The resulting solution was maintained at reflux overnight. The reaction mixture was cooled and concentrated under vacuum. The residue was washed with 3000 mL of hexane and filtered to afford the title compound as a yellow solid.

Workup

  1. customInto a 10000 mL 4-necked, round bottomed flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was maintained
  4. temperatureat reflux overnight
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated under vacuum
  7. washThe residue was washed with 3000 mL of hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-dc493622cd0b423abfbe2b9958f3c4b2
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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