4-Toluenesulfonyl chloride → HCID 57522713, 화합물

HRID 707196노트

반응식

HRID 707196 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 57522713HCID 57522713, 화합물수율 67.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-97fbf5b8e7ea461585224341a68dc0a6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175002B2

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