L-Alanine → HCID 10266974, compound

HRID 1271654Notes

Reaction equation

HRID 1271654 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[S:15]([OH:18])(=[O:17])=[O:16]>C(O)C>[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[S:15]([OH:18])(=[O:17])=[O:16].[CH2:7]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH2:1])[CH3:8]

Participants

4

Reactant 2

HCID 5950L-AlanineHCID 69382,4-Dimethylbenzenesulfonic acid

Product 1

HCID 10266974HCID 10266974, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

L-alanine (1.50 g, 16.84 mmol) and 2,4-dimethylbenzenesulfonic acid (2,4-DMBS) (3.76 g, 20.20 mmol) were added to ethanol (15 ml), and the mixture was heated overnight at 70 EC to perform esterification. To complete the esterification reaction, the mixture was heated to 90 EC, and ethanol (200 ml) was added over 3.5 hours, while distilling away almost the same amount of ethanol. Thereafter, the solvent was evaporated under reduced pressure, and the residue was dried under reduced pressure. The obtained oily residue was cooled in a refrigerator to allow partial crystallization. Diethyl ether (2.5 ml) and ethyl acetate (17.5 ml) were added, and the residue was dissolved almost entirely at 50° C. The mixture 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 3.00 g of L-alanine ethyl ester 2,4-dimethylbenzenesulfonate (L-Ala-OEt 2,4-DMBS salt) dry crystals (L-Ala-OEt 2,4-DMBS salt content 99.6%, 9.84 mmol, yield 58.4%).

Workup

  1. temperaturethe mixture was heated overnight at 70 EC
  2. customthe esterification reaction
  3. additionwas added over 3.5 hours
  4. distillationwhile distilling away almost the same amount of ethanol
  5. customThereafter, the solvent was evaporated under reduced pressure
  6. customthe residue was dried under reduced pressure
  7. temperatureThe obtained oily residue was cooled in a refrigerator
  8. customcrystallization
  9. additionDiethyl ether (2.5 ml) and ethyl acetate (17.5 ml) were added
  10. dissolutionthe residue was dissolved almost entirely at 50° C
  11. customto give a slurry
  12. temperatureThis slurry was cooled overnight in a refrigerator
  13. customthe crystals were separated
  14. customdried

Sources & evidence

ORD record
ord-6d4da30b083d450d8eedbd99071e6b0c
Source dataset
uspto-grants-2007_04
Patent number
US07205433B2

Reaction notes

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