1,4-Dioxane → (S)-3-amino-2-(4-chlorophenyl)propanoic acid hydrochloride
Reaction equation
Cl.O1CCOCC1.C(OC([NH:15][CH2:16][C@H:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:18]([OH:20])=[O:19])=O)(C)(C)C.O1CCOCC1>C(Cl)Cl>[ClH:27].[NH2:15][CH2:16][C@H:17]([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[C:18]([OH:20])=[O:19]Participants
Procedure
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.
Workup
- concentrationafter which it was concentrated
- additionThe resulting cloudy mixture was diluted with ether
- concentrationthe mixture was concentrated again
- additionThe mixture was diluted again with ether (20 mL)
- customthe solids were isolated by filtration through a medium frit funnel with nitrogen pressure
- washrinsed with ether (5×10 mL)
- customdried under nitrogen pressure
- customdried in vacuo
Sources & evidence
- ORD record
- ord-63049bd5d23a45f495b5ebd6c5289744
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150548B2
Reaction notes
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