Lithium Hydroxide → 4-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid
Reaction equation
[OH-].[Li+].[C:3]1([S:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])(=[O:15])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([S:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:15])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1Participants
Procedure
Lithium hydroxide (1.58 g, 65.9 mmol) was added to a solution of methyl 4-(1-(naphthalene-1-ylsulfonyl)piperidine-2-yl)butanoate 3 (4.95 g, 13.18 mmol) in methanol/water (54 ml/36 ml) and the reaction mixture was stirred at room temperature overnight. The completeness of the reaction was checked by means of TLC. When the reaction was complete, the methanol was distilled off under reduced pressure and ethyl acetate was added to the residue. The mixture was acidified with dilute HCl. The aqueous phase was extracted 2× with ethyl acetate and the combined organic phases were dried over Na2SO4 and concentrated under reduced pressure to obtain the desired product 4-(1-(naphthalene-1-ylsulfonyl)piperidine-2-yl)butanoic acid (AC-21) (4.38 g, 91%).
Workup
- distillationthe methanol was distilled off under reduced pressure and ethyl acetate
- additionwas added to the residue
- extractionThe aqueous phase was extracted 2× with ethyl acetate
- dry with materialthe combined organic phases were dried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cde0d2e1b6a446cbb2e83ad3f06f7d78
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318769B2
Reaction notes
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