Water → HCID 86650593, compound

HRID 1257398Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([CH3:25])=[C:15]([CH2:17][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:16]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C([Li])CCC.CN(C)[CH:33]=[O:34].O>O1CCCC1>[CH3:25][C:14]1[S:13][C:12]([C:4]2[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=2)[CH:33]=[O:34])=[N:16][C:15]=1[CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

Participants

Conditions

Temperature: -78 °C

Procedure

Under a nitrogen atmosphere at −78° C., to a solution (80 mL) of the compound (7.3 g, 17 mmol) obtained in Example 95a in tetrahydrofuran was added n-butyllithium (1.6M hexane solution, 16 mL, 25 mmol), and the mixture was stirred at the same temperature for 1 hr. Anhydrous N,N-dimethylformamide (2.6 mL, 33 mmol) was added to the reaction mixture, and the mixture was stirred overnight while allowing to spontaneously warm to room temperature from −78° C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20) to give the title compound (1.6 g, 24%) as an orange oil.

Workup

stirringthe mixture was stirred overnight
extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20)

Sources & evidence

ORD record: ord-52fee35fbd284d17a9b2a696eb58af8b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461348B2

Reaction notes

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