Potassium Hydroxide → (s)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoic acid
Reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([O:17][C@@H:18]([C:23]([O:36][CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([O:21]C)=[O:20])[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([O:17][C@@H:18]([C:23]([O:36][CH3:37])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:19]([OH:21])=[O:20])[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the compound of Example 13 (1.17 g, 2.34 mmol) in methanol (20 mL) is added a solution of potassium hydroxide (0.987 g, 23.4 mmol) in water (10 mL) and the reaction stirred at reflux for 5 hr. The reaction is cooled to room temperature and the methanol removed under reduced pressure on a rotary evaporator. The aqueous residue is washed with ethyl acetate (2×25 mL) and then the pH is adjusted to 2-3 with 2N HCl. The aqueous phase is extracted with ether (2×50 mL) to yield the title compound (0.997 g, 88%).
Workup
- temperatureat reflux for 5 hr
- customthe methanol removed under reduced pressure on a rotary evaporator
- washThe aqueous residue is washed with ethyl acetate (2×25 mL)
- extractionThe aqueous phase is extracted with ether (2×50 mL)
Sources & evidence
- ORD record
- ord-52473380a10746a7b397cfb33ad82d2d
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217155B2
Reaction notes
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