Benzyl chloroformate → (2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid
Reaction equation
[NH2:1][C@@H:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]>[OH-].[K+].O>[CH2:12]([O:11][C:9]([NH:1][C@@H:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
10 g of 2(S)-aminobutyric acid (97 mmol) are dissolved in aqueous 4M KOH solution (100 ml) and the mixture is cooled to 0° C. 24.7 g of benzyl chloroformate (145 mmol) are added and the mixture is stirred while allowing its temperature to rise to room temperature over 2 hours 30 minutes. The mixture is then diluted with water (100 ml) and extracted with ether (2×200 ml). The aqueous phase is acidified to a pH<1 with concentrated HCl and is extracted with ethyl acetate (3×200 ml). The ethyl acetate fractions are combined and dried (Na2SO4) and the solvent is removed. A white solid is obtained.
Workup
- extractionextracted with ether (2×200 ml)
- extractionis extracted with ethyl acetate (3×200 ml)
- dry with materialdried (Na2SO4)
- customthe solvent is removed
- customA white solid is obtained
Sources & evidence
- ORD record
- ord-13b2943d2c3d4a2fb5ba029dd4125aa6
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403561B1
Reaction notes
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