Hydrochloric Acid → (2S)-2-amino-2-phenylpropanoic acid hydrochloride
Reaction equation
C([NH:3][C@:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:5]([OH:7])=[O:6])=O.[ClH:15]>>[ClH:15].[NH2:3][C@:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:5]([OH:7])=[O:6]Participants
3
Procedure
The product of Example 445B (1.25g, 7.6 mmol)) in 1N HCl (12.5 mL) was refluxed for 1 hour. The reaction mixture was concentrated and dried at 40° C. under vacuum overnight to give (S)-2-amino-2-phenylpropanoic acid hydrochloride as a pale brown crystal (1.53 g). The intermediate amino acid (1.5 g. 7.5 mmol) was dissolved in EtOH (30 mL) was reacted with thionyl chloride (2.7 ml., 37.5 mmol) dropwise at room temperature then refluxed for 23 hours. The reaction was concentrated and the residue was partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer was washed with water (3×15 mL) and 10% aqueous NaHCO3 (1×15 mL), dried over MgSO4, concentrated to give the title compound (1.28 g, 90%).
Workup
- concentrationThe reaction mixture was concentrated