(Isocyanoimino)triphenylphosphorane → N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide
反応式
[N+:1]([N:3]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[C-:2].[C:23]1([CH2:33][C:34]([NH:36][C:37]2[CH:41]=[CH:40][S:39][C:38]=2[C:42]([OH:44])=O)=[O:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[O:44]1[CH:2]=[N:1][N:3]=[C:42]1[C:38]1[S:39][CH:40]=[CH:41][C:37]=1[NH:36][C:34](=[O:35])[CH2:33][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1参加物
4
実験手順
To a solution of (isocyanoimino)triphenylphosphorane (978 mg, 3.24 mmol) in anhydrous CH2Cl2 (30 mL) was added dropwise a solution of 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid (340 mg, 1.09 mmol) in anhydrous CH2Cl2 (27 mL). The resulting mixture was stirred at room temperature under nitrogen overnight and evaporated under reduced pressure. Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane) gave N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (45 mg, 12%). Method [7] m/z 357.9 (M+Na); retention time=5.919. 1H-NMR (CDCl3) δ 8.18 (d, J=1.1 Hz, 1H), 8.16 (d, J=1.4 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.61-7.41 (m, 5H), 4.27 (s, 2H).