2,4-Dimethylbenzenesulfonic acid → HCID 10401908, compound

HRID 1271657Notes

Reaction equation

HRID 1271657 reaction equation
[NH2:1][C@H:2]([C:4]([O:6][CH3:7])=[O:5])[CH3:3].Cl.[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[S:17]([OH:20])(=[O:19])=[O:18]>C(OC)(=O)C>[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[S:17]([OH:20])(=[O:19])=[O:18].[CH3:7][O:6][C:4](=[O:5])[C@H:2]([CH3:3])[NH2:1]

Participants

4

Reactant 2

HCID 69382,4-Dimethylbenzenesulfonic acidHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 10401908HCID 10401908, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent

Procedure

L-Ala-OMe HCl salt (0.68 g, 4.87 mmol) was suspended in methyl acetate (15 ml). 2,4-Dimethylbenzenesulfonic acid (2,4-DMBS) (1.09 g, 5.85 mmol) was added, and the mixture was stirred for dissolution. This solution was concentrated under reduced pressure, methyl acetate (15 ml) was added, and the mixture was concentrated twice under reduced pressure. The obtained concentrate was cooled in a refrigerator. Since partial crystallization occurred, methyl acetate (5 ml) and diethyl ether (15 ml) were added to dissolve the crystals by stirring at room temperature. This solution was stirred under ice-cooling to give a slurry. This slurry was cooled overnight in a refrigerator, and the crystals were separated and dried to give 1.18 g of L-alanine methyl ester 2,4-dimethylbenzenesulfonate (L-Ala-OMe 2,4-DMBS salt) dry crystals (L-Ala-OMe 2,4-DMBS salt 92.9%, 4.11 mmol, yield 84.4%).

Workup

  1. concentrationThis solution was concentrated under reduced pressure, methyl acetate (15 ml)
  2. additionwas added
  3. concentrationthe mixture was concentrated twice under reduced pressure
  4. concentrationThe obtained concentrate
  5. temperaturewas cooled in a refrigerator
  6. customSince partial crystallization
  7. additionmethyl acetate (5 ml) and diethyl ether (15 ml) were added
  8. dissolutionto dissolve the crystals
  9. stirringby stirring at room temperature
  10. stirringThis solution was stirred under ice-
  11. temperaturecooling
  12. customto give a slurry
  13. temperatureThis slurry was cooled overnight in a refrigerator
  14. customthe crystals were separated
  15. customdried

Sources & evidence

ORD record
ord-d9bbb4797b80465b9221a3574a484780
Source dataset
uspto-grants-2007_04
Patent number
US07205433B2

Reaction notes

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