Dichloromethane → 3-(5,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylic acid hydrochloride
Reaction equation
C([O:5][C:6](=[O:20])[CH:7]=[CH:8][C:9]1[CH:19]=[N:18][C:12]2[NH:13][CH2:14][CH2:15][O:16][CH2:17][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:29]>>[ClH:29].[N:18]1[C:12]2[NH:13][CH2:14][CH2:15][O:16][CH2:17][C:11]=2[CH:10]=[C:9]([CH:8]=[CH:7][C:6]([OH:20])=[O:5])[CH:19]=1Participants
Procedure
A suspension of 3-(5,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylic acid tert-butyl ester (0.14 g, 0.49 mmol) in CH2Cl2 (5 mL) was treated with TFA (5 mL). After stirring at room temperature for 30 min, the clear tan solution was concentrated in vacuo. The resulting oil was triturated with hexanes (20 mL) until the oil was converted to a fine off-white solid. The solid was then suspended in anhydrous HCl in dioxane (2 mL, 4.0 M), sonicated and concentrated to about 1 mL. The suspension was treated with Et2O (20 mL), sonicated, isolated by filtration and dried under vacuum. Yield: 0.11 g (87%); 1H NMR (300 MHz, DMSO-d6) δ 8.40 (br s, 3H), 8.31-8.29 (m, 2H), 7.53 (d, J=16.0 Hz, 1H), 6.51 (d, J=16.0 Hz, 1H), 4.76 (s, 2H), 3.96-3.92 (m, 2H), 3.71-3.67 (m, 2H); ESI MS m/z 221 [C11H12N2O3+H]+
Workup
- concentrationthe clear tan solution was concentrated in vacuo
- customThe resulting oil was triturated with hexanes (20 mL) until the oil
- customsonicated
- concentrationconcentrated to about 1 mL
- additionThe suspension was treated with Et2O (20 mL)
- customsonicated
- customisolated by filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-6a90563b46b14dccbc0decabf54401f5
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318720B2
Reaction notes
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