4-Toluenesulfonyl chloride → HCID 57522713、化合物

HRID 707196ノート

反応式

HRID 707196 の反応式
CCN([CH2:6][CH3:7])CC.S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:9].[OH:19][CH2:20][CH2:21][N:22]1[C:31]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:38](=[O:39])[C:30]=2[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:40]>C(Cl)Cl>[C:6]([O:19][CH2:20][CH2:21][N:22]1[C:31]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:38](=[O:39])[C:30]=2[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:40])(=[O:9])[CH3:7]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 3344746-(2-Hydroxyethyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione

生成物 1

HCID 57522713HCID 57522713、化合物収率 67.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Et3N (34.7 mg, 0.343 mmol), CH3COOAg (57.2 mg, 0.343 mmol), and TsCl (65.4 mg, 0.343 mmol) were added to the solution of 18 (50 mg, 0.172 mmol) in CH2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 16 h, and then washed with sat. NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated, adsorbed onto SiO2, and purified by flash column chromatography (SiO2), eluting with EtOAc—CHCl3 (2:8) to afford the desired product as a red solid (38.5 mg, 67%): mp 221-224° C. IR (film) 1738, 1693, 1655, and 1506 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.75 (d, J=8.0 Hz, 1H), 8.37 (d, J=7.9 Hz, 1H), 7.75 (t, J=5.8 Hz, 2H), 7.67 (dd, J=1.1 and 5.8 Hz, 1H), 7.51-7.41 (m, 3H), 4.84 (t, J=6.2 Hz, 2H), 4.57 (t, J=6.1 Hz, 2H), 1.94 (s, 3H); probe-EI/CI-MS m/z (rel intensity) 334 (MH+, 100); HRMS (+EI/CI) calcd for M+: 333.1001. found: 333.1005; HPLC purity: 97.3% (MeOH, 100%), 98.0% (MeOH—H2O, 90:10).

後処理

  1. washwashed with sat. NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (SiO2)
  6. washeluting with EtOAc—CHCl3 (2:8)

出典と根拠

ORDレコード
ord-97fbf5b8e7ea461585224341a68dc0a6
出典データセット
uspto-grants-2015_11
特許番号
US09175002B2

反応ノート

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