Sodium Hydroxide → HCID 136078238, compound

HRID 2378063Notes

Reaction equation

[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3([C:29]([O:31]C)=[O:30])[CH2:28][CH2:27]3)[O:17][N:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[OH-].[Na+]>O1CCCC1.O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]3)[O:17][N:16]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution consisting of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (Example 1, Compound D, 10 g) in tetrahydrofuran (100 mL) is added a 50 wt % sodium hydroxide in water solution (10 mL). The mixture is heated to 60° C. for 18 hours. The reaction mixture is concentrated under reduced pressure and partitioned between diethyl ether and water. The aqueous layer is washed with diethyl ether and acidified to pH 5 with concentrated aqueous hydrochloric acid. The aqueous phase is extracted with ethyl acetate. The combined extracts are washed with water and brine solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the title compound (5.64 g); MS (APCI+) m/z 322 (MH+.)

Workup

concentrationThe reaction mixture is concentrated under reduced pressure
custompartitioned between diethyl ether and water
washThe aqueous layer is washed with diethyl ether
extractionThe aqueous phase is extracted with ethyl acetate
washThe combined extracts are washed with water and brine solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-18f1a7ab0a3e4143b71a10c6a1c8d655
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470715B2

Reaction notes

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