1,4-Dioxane → (S)-3-amino-2-(4-chlorophenyl)propanoic acid hydrochloride

4M HCl/dioxane (5.49 mL, 22.0 mmol) was added to a solution of (S)-3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoic acid (0.329 g, 1.10 mmol) in 2:1 dioxane:DCM (10 mL). The reaction mixture was stirred at room temperature overnight (16 hours), after which it was concentrated to ⅓ volume. The resulting cloudy mixture was diluted with ether, and the mixture was concentrated again to ⅓ volume. The mixture was diluted again with ether (20 mL), and the solids were isolated by filtration through a medium frit funnel with nitrogen pressure. The solids were rinsed with ether (5×10 mL), dried under nitrogen pressure, and dried in vacuo to give (S)-3-amino-2-(4-chlorophenyl)propanoic acid hydrochloride (0.199 g, 76.8% yield) as a white powder. HPLC>99 area % pure. LC/MS (APCI+) m/z 200.

1. concentrationafter which it was concentrated
2. additionThe resulting cloudy mixture was diluted with ether
3. concentrationthe mixture was concentrated again
4. additionThe mixture was diluted again with ether (20 mL)
5. customthe solids were isolated by filtration through a medium frit funnel with nitrogen pressure
6. washThe solids were rinsed with ether (5×10 mL)
7. customdried under nitrogen pressure
8. customdried in vacuo

ORD record

ord-cda1c5c33af646fd822aae4be9bfc829

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003651B2