Imidazole → HCID 11000905, compound

HRID 388728Notes

Reaction equation

[CH:1](=[C:3]1/[CH2:4][CH2:5][C@@H:6]2[C@:11]/1([CH3:12])[CH2:10][CH2:9][CH2:8][C@@H:7]2[OH:13])\[CH3:2].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C)C=O>[C:22]([Si:19]([O:13][C@H:7]1[CH2:8][CH2:9][CH2:10][C@@:11]2([CH3:12])[C@H:6]1[CH2:5][CH2:4]/[C:3]/2=[CH:1]/[CH3:2])([CH3:21])[CH3:20])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 60 °C

Procedure

The compound of Example 8A (0.74 g, 4.1 mmol) was dissolved in 4 mL of dimethylformamide; 0.4 g of imidazole was added, followed by 0.7 g of tert-butyldimethylsilyl chloride. The resultant mixture was stirred at ambient temperature for 4 hours; equal portions of tert-butyldimethylsilyl chloride and imidazole were added, and the mixture was heated overnight at 60° C. Water was added; the mixture was stirred at ambient temperature for 30 minutes, and then extracted with ether. The organic phase was washed sequentially with 1 N aqueous H3PO4, water, and brine, and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 0% to 10% ethyl acetate in hexanes. The titled compound was isolated contaminated with some unreacted starting material (0.31 g, 42%).

Workup

extractionextracted with ether
washThe organic phase was washed sequentially with 1 N aqueous H3PO4, water, and brine
dry with materialdried over Na2SO4
customThe solvents were removed in vacuo
customthe residue was purified by chromatography on an Analogix Intelliflash 280™
washeluting with a gradient of 0% to 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-d9719c641ccd47239404a10b7e5c99b5
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377913B2

Reaction notes

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