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, 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. washrinsed with ether (5×10 mL)
7. customdried under nitrogen pressure
8. customdried in vacuo

ORD record

ord-a533cb9dfdd546c4a2ee3a876a61a81f

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359340B2