L-Alanine → HCID 10401174, compound
Reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].O.[C:8]1([S:14]([OH:17])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[C:8]1([S:14]([OH:17])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:8]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH2:1])[CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
L-alanine (1.50 g, 16.84 mmol) and benzenesulfonic acid monohydrate (BsOH H20) (3.56 g, 20.20 mmol) were added to ethanol (10 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. Ethanol (0.5 ml) and diethyl ether (30 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 4.55 g of L-alanine ethyl ester benzenesulfonate (L-Ala-OEt BsOH salt) dry crystals (L-Ala-OEt BsOH salt content 87.6%, (14.47 mmol), yield 86.0%).
Workup
- customthe esterification reaction
- temperaturethe mixture was heated to 90° C.
- distillationwhile distilling away almost the same amount of ethanol
- customThereafter, the solvent was evaporated under reduced pressure
- customthe residue was dried under reduced pressure
- additionEthanol (0.5 ml) and diethyl ether (30 ml) were added
- customto partially crystallize an oily residue
- customto give a slurry
- temperatureThis slurry was cooled overnight in a refrigerator
- customthe crystals were separated
- customdried
Sources & evidence
- ORD record
- ord-eb75df2a89614cd6822c4fa6f0b84328
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07205433B2
Reaction notes
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