1-Butanol → HCID 11595894, compound

HRID 2299221Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].S(=O)(=O)(O)O.[CH2:29](O)[CH2:30]CC>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH2:23][CH2:29][CH3:30])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:11])=[O:12]

Participants

Conditions

Temperature: 82.5 °C

Procedure

To a solution of ethyl 6-[N-(2,4difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate obtained in Example 3 (Compound 3, 180 mg) in 1-butanol (5 ml), a concentrated sulfuric acid (0.12 ml) was added and the mixture was stirred at 80 to 85° C. for 7 days. After cooling, the reaction mixture was diluted with ethyl acetate (60 ml) and washed with water (60 ml). The ethyl acetate layer was washed with water (60 ml×5), dried over anhydrous magnesium sulfate and then evaporated under reduced pressure to dryness. The residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/4) and then crystallized from diisopropyl ether to yield butyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 33, 52 mg) as white crystals.

Workup

temperatureAfter cooling
washwashed with water (60 ml)
washThe ethyl acetate layer was washed with water (60 ml×5)
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure to dryness
customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/4)
customcrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-e3d7b225793c4b04bc892a5c582ee182
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495604B1

Reaction notes

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