L-Alanine → HCID 10063562, compound

HRID 1271655Notes

Reaction equation

HRID 1271655 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[S:15]([OH:18])(=[O:17])=[O:16]>C(O)C>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[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 118682,5-Dimethylbenzenesulfonic acid

Product 1

HCID 10063562HCID 10063562, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

L-alanine (1.50 g, 16.84 mmol) and 2,5-dimethylbenzenesulfonic acid (2,5-DMBS) (3.76 g, 20.20 mmol) were added to ethanol (15 ml), and the mixture was heated overnight at 70° C. to perform esterification. To complete the esterification reaction, the mixture was heated to 90° C., 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. Ethyl acetate (7 ml) was added, and the residue was dissolved almost entirely at 50° C. The mixture was stirred at room temperature, diethyl ether (40 ml) was further added, and the mixture was stirred at room temperature to give a slurry. The obtained slurry was cooled overnight in a refrigerator, and the crystals were separated and dried to give 3.77 g of L-alanine ethyl ester 2,5-dimethylbenzenesulfonate (L-Ala-OEt 2,5-DMBS salt) dry crystals (L-Ala-OEt 2,5-DMBS salt content 95.6%,11.88 mmol, yield 70.5%).

Workup

  1. customthe esterification reaction
  2. temperaturethe mixture was heated to 90° C.
  3. distillationwhile distilling away almost the same amount of ethanol
  4. customThereafter, the solvent was evaporated under reduced pressure
  5. customthe residue was dried under reduced pressure
  6. temperatureThe obtained oily residue was cooled in a refrigerator
  7. customcrystallization
  8. additionEthyl acetate (7 ml) was added
  9. dissolutionthe residue was dissolved almost entirely at 50° C
  10. additiondiethyl ether (40 ml) was further added
  11. stirringthe mixture was stirred at room temperature
  12. customto give a slurry
  13. temperatureThe obtained slurry was cooled overnight in a refrigerator
  14. customthe crystals were separated
  15. customdried

Sources & evidence

ORD record
ord-39876a7fbb624d0a9dcb3f373af3c8f2
Source dataset
uspto-grants-2007_04
Patent number
US07205433B2

Reaction notes

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