2,5-Dimethylbenzenesulfonic acid → HCID 10266174, compound

HRID 1271658Notes

Reaction equation

HRID 1271658 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]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[S:17]([OH:20])(=[O:19])=[O:18]>C(OC)(=O)C>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[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 118682,5-Dimethylbenzenesulfonic acidHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 10266174HCID 10266174, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent

Procedure

L-Ala-OMe HCl salt (1.00 g, 7.16 mmol) was suspended in methyl acetate (15 ml). 2,5-Dimethylbenzenesulfonic acid (2,5-DMBS) (1.60 g, 8.59 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 to allow crystallization. Methyl acetate (15 ml) was added to dissolve the obtained slurry almost entirely at 50° C. This solution was stirred at room temperature to give a slurry. This slurry was cooled overnight in a refrigerator, and the crystals were separated and dried to give 1.87 g of L-alanine methyl ester 2,5-dimethylbenzenesulfonate (L-Ala-OMe 2,5-DMBS salt) dry crystals (L-Ala-OMe 2,5-DMBS salt content 98.9%, 6.23 mmol, yield 87.0%).

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. customcrystallization
  5. additionMethyl acetate (15 ml) was added
  6. dissolutionto dissolve the obtained slurry almost entirely at 50° C
  7. stirringThis solution was stirred at room temperature
  8. customto give a slurry
  9. temperatureThis slurry was cooled overnight in a refrigerator
  10. customthe crystals were separated
  11. customdried

Sources & evidence

ORD record
ord-9051643683d04209aad67d95debd92ba
Source dataset
uspto-grants-2007_04
Patent number
US07205433B2

Reaction notes

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