Dansyl chloride → N-Dansyl-3,5-di-(3-methylmaleimido)aniline

HRID 76769

反応式

HRID 76769 の反応式
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].FC(F)(F)C([O-])=O.[CH3:25][C:26]1[C:31](=[O:32])[N:30]([C:33]2[CH:34]=[C:35]([CH:37]=[C:38]([N:40]3[C:44](=[O:45])[C:43]([CH3:46])=[CH:42][C:41]3=[O:47])[CH:39]=2)[NH3+:36])[C:28](=[O:29])[CH:27]=1>N1C=CC=CC=1>[S:1]([NH:36][C:35]1[CH:37]=[C:38]([N:40]2[C:44](=[O:45])[C:43]([CH3:46])=[CH:42][C:41]2=[O:47])[CH:39]=[C:33]([N:30]2[C:31](=[O:32])[C:26]([CH3:25])=[CH:27][C:28]2=[O:29])[CH:34]=1)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2]

参加物

4

反応物 2

HCID 11801Dansyl chlorideHCID 68007149HCID 68007149、化合物

生成物 1

HCID 50918100N-Dansyl-3,5-di-(3-methylmaleimido)aniline収率 16%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

反応条件

温度
25 °C

実験手順

Dansyl chloride (139 mg, 0.517 mmol) in pyridine (3 mL) was added to a pyridine solution of 4 (200 mg, 0.517 mmol). The resulting mixture was stirred at 25° C. for 18 hours after which the volatiles were evaporated under reduced pressure. The resulting oil was taken back in CHCl3 and the organic phase was washed with aqueous saturated Na2CO3, dried over MgSO4 and evaporated. The crude was purified by flash chromatography on silica gel (Tol/EtOAc 10%) giving 5 as a light green solid (40 mg, 0.074 mmol, 16%). 1H NMR (400 MHz, (CD3)2CO) δ 9.71 (s, 1H), 8.56 (d, J=8.4 Hz, 1H), 8.51 (d, J=8.8 Hz, 1H), 8.39 (dd, J1=1.2, 7.2 Hz, 1H), 7.62-7.58 (td, J=1.2, 7.2 Hz, 2H), 7.28-7.27 (m, 3H), 7.11 (t, J=2.0 Hz, 1H), 6.63-6.61 (m, 2H); 13C NMR (75 MHz, (CD3)2CO) δ 171.3, 170.4, 152.8, 135.4, 134.0, 131.7, 131.5, 130.3, 130.2, 129.6, 128.7, 124.9, 119.8, 119.6, 116.6, 115.9, 46.3, 12.1; HRMS (ESI) Calculated for C28H25N4O6S [M+H]+: 545.1516. Found: 545.1489. m.p.: 230° C.

後処理

  1. customwere evaporated under reduced pressure
  2. washthe organic phase was washed with aqueous saturated Na2CO3
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (Tol/EtOAc 10%)

出典と根拠

ORDレコード
ord-dd771b82ecab4068b86c1072bfaa75c4
出典データセット
uspto-grants-2014_09
特許番号
US08835641B2

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