反応式
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=O.[NH2:10][C:11]1[S:12][C:13]2[CH2:22][CH2:21][CH2:20][CH2:19][C:14]=2[C:15]=1[C:16](N)=[O:17]>S(Cl)(Cl)=O.O1CCOCC1.O>[CH3:9][O:8][C:1](=[O:7])[CH2:2][CH2:3][C:4]([NH:10][CH:11]1[S:12][C:13]2[CH2:22][CH2:21][CH2:20][CH2:19][C:14]=2[C:15]1=[C:16]=[O:17])=[O:6]参加物
実験手順
Monomethyl hydrogen succinate (4.7 g, 0.035 mol) was refluxed in thionyl chloride (20 ml) for 2 hrs. After consumption of starting material, excess of thionyl chloride was distilled off. The reaction mixture dissolved in dioxane (10 ml) and was added drop wise to 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide 1 (7 g, 0.035 moles) in dioxane (10 ml) at 0° C. and stirred at room temperature (R.T) for 2 hrs. The reaction mixture was diluted with water to give crude product which was filtered and washed with water. The crude was purified by chromatography on silica gel using 1:1 Ethyl acetate:Hexane to give 5 g (46%) of N-(3-carbonyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-succinamic acid methyl ester. 1H NMR (400 MHz, DMSO) δ ppm=1.72 (m, 4H), 2.6 (m, 4H), 2.68 (m, 4H), 3.59 (s, 3H), 6.99 (s, 1H), 7.55 (s, 1H), 11.48 (s, 1H). LC-MS: [M−H]=308.9.
後処理
- customAfter consumption of starting material
- distillationexcess of thionyl chloride was distilled off
- dissolutionThe reaction mixture dissolved in dioxane (10 ml)
- customto give crude product which
- filtrationwas filtered
- washwashed with water
- customThe crude was purified by chromatography on silica gel using 1:1 Ethyl acetate
出典と根拠
- ORDレコード
- ord-97e473ca689a4404bc45d53705fd6edd
- 出典データセット
- uspto-grants-2016_07
- 特許番号
- US09399647B2
関連ノート
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