Dichloromethane → (E)-3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylic acid hydrochloride
反応式
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:13](/[CH:15]=[CH:16]/[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:14][C:4]=2[CH2:3]1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:32]>>[ClH:32].[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:14][C:4]=2[CH2:3]1参加物
実験手順
A suspension of (E)-tert-butyl 3-(5-methyl-4-oxo-1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)acrylate (391 mg, 1.23 mmol) in CH2Cl2 (10 mL) was treated with TFA (10 mL). After stirring at room temperature for 2 h, the solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl in dioxane (4 mL, 4.0 M) and sonicated until the oil was converted to a fine off-white solid. After stirring for 20 min, the suspension was concentrated. The solid was washed with Et2O, isolated by filtration and dried under vacuum. Yield: 388 mg (quant); 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.04 (s, 1H), 7.48 (d, J=16.0 Hz, 1H), 6.48 (d, J=16.0 Hz, 1H), 4.78 (bs, 1H), 3.90 (s, 2H), 2.99 (s, 2H), 2.79 (s, 2H), 2.58 (s, 3H); ESI MS m/z 298 [C13H15N3O3+H]+
後処理
- concentrationthe solution was concentrated in vacuo
- additionThe resulting oil was treated with anhydrous HCl in dioxane (4 mL, 4.0 M)
- customsonicated until the oil
- stirringAfter stirring for 20 min
- concentrationthe suspension was concentrated
- washThe solid was washed with Et2O
- customisolated by filtration
- customdried under vacuum
出典と根拠
- ORDレコード
- ord-3e6e17abe52241808b1add10d8e48a23
- 出典データセット
- uspto-grants-2012_11
- 特許番号
- US08318720B2
反応ノート
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