Acetic Acid → HCID 69899494, compound

HRID 1884233Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:35])[C:19]([C:25]2[CH:34]=[CH:33][C:32]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=3[CH:26]=2)=[CH:20][O:21][CH:22]([F:24])[F:23])=[CH:11][C:10]=1[O:36][CH3:37])C1C=CC=CC=1.Br.C(O)(=O)C>O>[F:23][CH:22]([F:24])[O:21][CH:20]=[C:19]([C:25]1[CH:34]=[CH:33][C:32]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=1)[C:18]([NH:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:36][CH3:37])[CH:11]=1)=[O:35]

Participants

Conditions

Temperature: 80 °C

Procedure

2.40 g (4.73 mmol) of N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-3-difluoromethoxy-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide, 1.20 g (7.09 mmol) of 48% hydrobromic acid and 30 ml of acetic acid were mixed and stirred at 80° C. for 2 hours. Water was added to to the reaction mixture, which was followed by extracted with ethyl acetate, 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 column chromatography (eluent, hexane:ethyl acetate=1:1) to give 1.81 g of 3-difluoromethoxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (the present compound 1371).

Workup

extractionby extracted with ethyl acetate
washwashed with 5% hydrochrolic acid and saturated brine subsequently
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-24203628fc254ded8b9b241ab3364979
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762321B2

Reaction notes

Loading…