Acetyl chloride → HCID 69899127, compound

HRID 1884231Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[F:5][CH:6]([F:34])[O:7][CH:8]=[C:9]([C:24]1[CH:33]=[CH:32][C:31]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=1)=[O:11].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C.O>[F:5][CH:6]([F:34])[O:7][CH:8]=[C:9]([C:24]1[CH:33]=[CH:32][C:31]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:1](=[O:3])[CH3:2])=[C:17]([O:22][CH3:23])[CH:16]=1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Eighty milligrams (80 mg) of acetyl chloride (1.00 mmol) were added to a mixture of 420 mg (1.00 mmol), of 3-difluoromethoxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl) acrylamide, 120 mg (1.20 mmol) of triethylamine and 5 ml of tetrahydrofuran at 0° C. and stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. Water and ethyl acetate were added to the reaction mixture. The organic layer was washed with 5% hydrochrolic acid and saturated brine subsequently, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (eluent, hexane:ethyl acetate=3:1) to give 260 mg of 3-difluoromethoxy-N-[2-(3-methoxy-4-acetyloxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (the present compound 1282).

Workup

waitat room temperature for 2 hours
washThe organic layer was washed with 5% hydrochrolic acid and saturated brine subsequently
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-604613f9c45042b3add004daae695f29
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762321B2

Reaction notes

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