Sodium hydride → HCID 90416509, compound

HRID 633536Notes

Reaction equation

[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[H-].[Na+].F[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][C:15]=1[C:24]1[C:32]2[C:27](=[C:28]([O:33][CH3:34])[N:29]=[CH:30][CH:31]=2)[N:26]([CH3:35])[CH:25]=1>O1CCCC1>[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][C:15]=2[C:24]2[C:32]3[C:27](=[C:28]([O:33][CH3:34])[N:29]=[CH:30][CH:31]=3)[N:26]([CH3:35])[CH:25]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (4,4-difluorocyclohexyl)methanol (0.156 g, 1.04 mmol) in anhydrous tetrahydrofuran (4.33 mL) under nitrogen was treated with sodium hydride (0.042 g, 1.040 mmol) at ambient temperature, stirred for 10 minutes, treated with the product from Example 17C (0.087 g, 0.26 mmol) and heated under nitrogen at 60° C. for 18 hours. The mixture was cooled and partitioned into ethyl acetate/water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-60% ethyl acetate in heptanes) afforded the title compound (0.1 g, 83%).

Workup

temperatureThe mixture was cooled
custompartitioned into ethyl acetate/water
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried (anhydrous Na2SO4)
filtrationfiltered
concentrationconcentrated
customPurification by chromatography (silica gel, 0-60% ethyl acetate in heptanes)

Sources & evidence

ORD record: ord-b235236f591040ad9765bad099ecec6f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

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