Acetone → (2S,3S)-3-Amino-2-hydroxy-4-phenylbutyric acid hydrochloride
Reaction equation
C1(N[C:5]([C@H:7]2[O:11]C(C(C)C)=[N:9][C@H:8]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:6])CC1.[ClH:22].CC(C)=[O:25]>>[ClH:22].[OH:11][C@@H:7]([C@@H:8]([NH2:9])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([OH:6])=[O:25]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
(4S,5S)—N-Cyclopropyl-2-isopropyl-4-benzyl-4,5-dihydro-1,3-oxazole-5-carboxamide (63 mg), acetone (2.5 ml) and concentrated hydrochloric acid (0.25 g) were mixed, and the mixture was stirred at 50° C. for 23 hours. The reaction mixture was concentrated, and isopropanol (5 ml) was added. The mixture was concentrated under reduced pressure. The same operation was further repeated, and then isopropanol (3 ml) was added to precipitate a crystal. The crystal was collected by filtration under reduced pressure, and was dried in vacuum to obtain the title compound as a white crystal (23 mg, yield: 36%).
Workup
- concentrationThe reaction mixture was concentrated
- additionisopropanol (5 ml) was added
- concentrationThe mixture was concentrated under reduced pressure
- additionisopropanol (3 ml) was added
- customto precipitate a crystal
- filtrationThe crystal was collected by filtration under reduced pressure
- customwas dried in vacuum
Sources & evidence
- ORD record
- ord-6435a0b5d3874dec88944226e293c0e2
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834190B2
Reaction notes
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