Potassium Phosphate, Tribasic → [(5S)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl butyrate
Reaction equation
[C:1]([O:6][CH2:7][CH:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=2)[CH2:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC(C)=O>[C:1]([O:6][CH2:7][C@H:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=2)[CH2:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4]Participants
Procedure
Racemic [3-(5-bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl butyrate (Intermediate 9, 80 g, 0.244 mol) was dissolved in acetone (4 L), and 0.1 M potassium phosphate buffer (pH˜7) (4 L) was added with vigorous stirring to give a clear yellow solution. PS-lipase (1.45 g, Sigma cat no L-9156) was added and the mixture was gently stirred at ambient temp. for 42 hrs. The solution was divided into 3 equal volumes of ˜2.6 L and each was extracted with dichloromethane (2×1 L), the pooled organic phases were dried over sodium sulfate and evaporated. The unreacted [(5S)-3-(5-bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl butyrate was isolated via flash column chromatography (9:1 hexane:ethyl acetate) as a clear yellow oil, 36.4 g (45.5%).
Workup
- customto give a clear yellow solution
- additionPS-lipase (1.45 g, Sigma cat no L-9156) was added
- stirringthe mixture was gently stirred at ambient temp. for 42 hrs
- extractioneach was extracted with dichloromethane (2×1 L)
- dry with materialthe pooled organic phases were dried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-ae0f3db645344bc7aea2ed1ad4145c32
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192974B2
Reaction notes
Loading…