Lithium Hydroxide → 4-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid
Reaction equation
[C:1]1([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Li+]>CO.O>[C:1]1([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Procedure
To a solution of methyl 4-(1-(naphthalene-1-ylsulfonyl)piperidin-2-yl)butanoate (Ester-12) (4.95 g, 13.18 mmol.) in Methanol/Water (54 ml/36 ml) lithiumhydroxide (1.58 g, 65.9 mmol) was added and the reaction mixture was stirred over night at room temperature. The completion of the reaction was controlled via thin-layer chromatography. After completion the methanol was evaporated in vacuum, and the residue was triturated with ethyl acetate. The mixture was made acidic with diluted HCl. The aqueous layer was extracted 2× with ethyl acetate, the combined organic layers were dried over sodium sulfate and were evaporated in vacuum to give the desired product 4-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid (AC-12) (4.38 g, 91%).
Workup
- customAfter completion the methanol was evaporated in vacuum
- customthe residue was triturated with ethyl acetate
- extractionThe aqueous layer was extracted 2× with ethyl acetate
- dry with materialthe combined organic layers were dried over sodium sulfate
- customwere evaporated in vacuum
Sources & evidence
- ORD record
- ord-74c260a7df214fe2976842cfa189d1f1
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268814B2
Reaction notes
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