Potassium Carbonate → HCID 23157358, compound

HRID 508018Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=2[CH3:19])=[CH:9][C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[O:25]1[C:27]2([CH2:32][CH2:31][S:30][CH2:29][CH2:28]2)[CH2:26]1.C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[C:1]([NH:4][C:5]1[C:10]([C:11]2[C:12]([CH3:19])=[CH:13][C:14]([O:18][CH2:26][C:27]3([OH:25])[CH2:32][CH2:31][S:30][CH2:29][CH2:28]3)=[CH:15][C:16]=2[CH3:17])=[CH:9][C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 6-(acetylamino)-4′-hydroxy-2′,6′-dimethylbiphenyl-3-carboxylate (490 mg, 1.50 mmol) and 1-oxa-6-thiaspiro[2.5]octane (224 mg, 1.72 mmol) in N,N-dimethylformamide (8 mL) was added potassium carbonate (238 mg, 1.72 mmol), and the mixture was stirred at 80° C. for 10 hr. Brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=2/3), and then by basic silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/2) to give the title compound (270 mg, yield 39%) as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=2/3)

Sources & evidence

ORD record: ord-7991119b975b4dd4baf175a318e4c77f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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