Hydrochloric Acid → HCID 86703745, compound

HRID 1849858Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:16][C:17]1[C:18](F)=[CH:19][C:20]([F:30])=[C:21]([CH:29]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].Cl>CS(C)=O>[Cl:16][C:17]1[C:18]([O:9][CH2:8][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])=[CH:19][C:20]([F:30])=[C:21]([CH:29]=1)[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (2-methylcyclohexyl)methanol (1.28 g, 9.99 mmol) in anhydrous dimethylsulfoxide (20 mL) was added cesium carbonate (5.87 g, 18.06 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (2.23 g, 8.96 mmol). The reaction mixture was stirred at 70° C. for 16 hours; cooled to ambient temperature and acidified to pH=1 with 5% aqueous hydrochloric acid solution and extracted with ethyl acetate (2×15 mL), the combined organics were washed with brine (15 mL); dried over anhydrous sodium sulfate; filtered and concentrated in vacuo. Purification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes) afforded the title compound (2.30 g, 72%); MS (ES+) m/z 303.2, 301.2 (M−54); MS (ES−) m/z 301.2, 299.2 (M−56).

Workup

temperaturecooled to ambient temperature
extractionextracted with ethyl acetate (2×15 mL)
washthe combined organics were washed with brine (15 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-3575068881c34b5dba3c977c0c437216
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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