反応式
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:8][CH2:7]1)=O)C>Br.O>[S:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[NH:12][CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1参加物
反応条件
- 温度
- -20 °C
実験手順
A solution of 4-(benzothiazol-2-ylamino)-piperidine-1-carboxylic acid ethyl ester (3.70 g, 12.0 mmol) in hydrobromic acid 48% in water (20 mL) was heated to reflux. After 18 h hydrobromic acid was removed under reduced pressure and the crude solid dissolved by vigorous stirring in hot methanol (50 mL). The obtained solution was cooled to −20° C. by which a precipitate formed that was removed by filtration. The organic phase was concentrated under reduced pressure, 4 N NaOH (100 mL) added and the solution extracted with dichloromethane (3×100 mL). The combined organic phases were dried over MgSO4 to yield after evaporation of the solvent 1.7 g (61%) of the title compound which was used directly in the following step. 1H NMR (300 MHz, DMSO): δ 1.19-1.39 (m, 2H), 1.90-2.00 (m, 2H), 2.92-2.97 (m, 2H), 3.72-3.79 (m, 2H), 6.99 (t, J=8.2 Hz, 1H), 7.20 (t, J=8.2 Hz, 1H), 7.37 (d, J=7.6 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.95 (d, J=7.2 Hz, 1H). MS (ISP): 233.9 [M+H]+.
後処理
- customAfter 18 h hydrobromic acid was removed under reduced pressure
- dissolutionthe crude solid dissolved
- customformed
- customthat was removed by filtration
- concentrationThe organic phase was concentrated under reduced pressure, 4 N NaOH (100 mL)
- additionadded
- extractionthe solution extracted with dichloromethane (3×100 mL)
- dry with materialThe combined organic phases were dried over MgSO4
- customto yield
- customafter evaporation of the solvent 1.7 g (61%) of the title compound which
出典と根拠
- ORDレコード
- ord-501016dbe4c2469ea996bff51d29f4ce
- 出典データセット
- uspto-grants-2010_01
- 特許番号
- US07645753B2
関連ノート
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