Sodium Hydroxide → 3-Phenoxy-3-phenyl-2-(4,6-dimethoxy-2-pyrimidinyl)oxybutyric acid

HRID 378364Notes

Reaction equation

[O:1]([C:8]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:25])[CH:9]([O:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=1)[C:10]([O:12]C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[O:1]([C:8]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([CH3:25])[CH:9]([O:14][C:15]1[N:16]=[C:17]([O:23][CH3:24])[CH:18]=[C:19]([O:21][CH3:22])[N:20]=1)[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.3 g of methyl 3-phenoxy-3-phenyl-2-(4,6-dimethoxy-2-pyrimidinyl)oxybutyrate (Example 6 change to 42) are dissolved in 20 ml of MeOH and 40 ml of THF, and 3.7 g of 10% NaOH solution are added. The mixture is stirred at 60° C. for 6 hours and at room temperature for 12 hours, the solvent is removed by distillation under reduced pressure, and the residue is taken up in 100 ml of water. Unreacted ester is extracted with ethyl acetate. The aqueous phase is then adjusted to pH 1-2 with dilute hydrochloric acid and extracted with ethyl acetate. Drying over magnesium sulfate and removal of the solvent by distillation result in 1.0 g of a white powder.

Workup

customthe solvent is removed by distillation under reduced pressure
extractionUnreacted ester is extracted with ethyl acetate
extractionextracted with ethyl acetate
dry with materialDrying over magnesium sulfate and removal of the solvent by distillation

Sources & evidence

ORD record: ord-3d3dc731e6354698b23bee6d73931025
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06030975

Reaction notes

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