L-Alanine → HCID 10425460, compound

HRID 1271652Notes

Reaction equation

HRID 1271652 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:12][CH:13]=1.[CH2:8]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH2:1])[CH3:9]

Participants

4

Reactant 2

HCID 5950L-AlanineHCID 7400p-Chlorobenzenesulfonic acid

Product 1

HCID 10425460HCID 10425460, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

L-alanine (1.50 g, 16.84 mmol) and 4-chlorobenzenesulfonic acid (4-CBS) (3.89 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. Ethanol (1 ml) and diethyl ether (60 ml) were added to partially crystallize an oily residue and 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 3.52 g of L-alanine ethyl ester 4-chlorobenzenesulfonate (L-Ala-OEt 4-CBS salt) dry crystals (L-Ala-OEt 4-CBS salt content 93.6%, 10.64 mmol, yield 63.2%).

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. additionEthanol (1 ml) and diethyl ether (60 ml) were added
  8. customto partially crystallize an oily residue
  9. customto give a slurry
  10. temperatureThis slurry was cooled overnight in a refrigerator
  11. customthe crystals were separated
  12. customdried

Sources & evidence

ORD record
ord-bce2ddfb36844af184e79257b8f750e7
Source dataset
uspto-grants-2007_04
Patent number
US07205433B2

Reaction notes

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