Triethylamine → 4-Ethylthio-3-(3-methanesulfonyloxy-1-propyl)-5-(4-methyl-1,2-dioxocyclobut-3-en-3-yl)amino indole

HRID 441102노트

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HRID 441102 반응식
[CH2:1]([S:3][C:4]1[C:12]([NH:13][C:14]2[C:15](=[O:20])[C:16](=[O:19])[C:17]=2[CH3:18])=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:7][NH:8]2)[CH3:2].CCN(CC)CC.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C1COCC1.C(Cl)Cl.C(Cl)Cl>[CH2:1]([S:3][C:4]1[C:12]([NH:13][C:14]2[C:15](=[O:20])[C:16](=[O:19])[C:17]=2[CH3:18])=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH2:21][CH2:22][CH2:23][O:24][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:7][NH:8]2)[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 224057163-(4-Ethylthio-5-(4-methyl-1,2-dioxocyclobut-3-en-3-yl)amino-3-indolyl)1-propanol

생성물 1

HCID 224056664-Ethylthio-3-(3-methanesulfonyloxy-1-propyl)-5-(4-methyl-1,2-dioxocyclobut-3-en-3-yl)amino indole

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21919333Tetrahydrofurane dichloromethane용매

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온도
23 °C

실험 절차

A cold (5° C.) mixture of 3-(4-ethylthio-5-(4-methyl-1,2-dioxocyclobut-3-en-3-yl) amino-3-indolyl)1-propanol (0.708 g, 2.1 mmol) and Et3N (0.697 ml, 5.0 mmol) in THF:CH2Cl2 (1:2, 45 ml) mixture kept under argon atm. was treated dropwise with MsCl (0.387 ml, 5.0 mmol) and stirred at 23° C. for 1.5 h. The reaction mixture was diluted with CH2Cl2 (40ml) and washed with H2O (10ml) and saturated NaHCO3 solution. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude material was purified on silica gel dry column using a mixture of CH2Cl2 :EtOAc (7.3) as eluting solvent. Appropriate fractions were concentrated in vacuo giving a yellow oil, 0.70 g, 79%. 1H NMR (DMSO-d6) δ (ppm): 11.26, 11.20, 10.81 and 10.53 (4 br s, 2H, indolic NH and 5-NH), 7.42 (br s, 1H), 7.32 (s, 1H), 7.09 (d, J=8.2 Hz, 1H), 4.27 (t, J=6.4 Hz, 2H, CH2OSO2), 3.17 (s, 3H, CH3SO2), 3.11 (t, J=7 Hz, 2H, CH2CH2CH2O), 2.67 (br s, 2H, CH3CH2S), 2.28 (br, s, 1H, CH3 of dioxocyclobutene), 2.0-2.15 (m, 2H, CH2CH2CH2O), 1.59 (br s, 2H CH3 of dioxocyclobutene), 0.9-1.1 (m, 3H, CH3CH2S). IR (film) n:3710, 3180, 1783, 1728, 1590, 1340 and 1170 cm-1.

후처리

  1. washwashed with H2O (10ml) and saturated NaHCO3 solution
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified on silica gel
  5. customdry column
  6. additiona mixture of CH2Cl2
  7. washEtOAc (7.3) as eluting solvent
  8. concentrationAppropriate fractions were concentrated in vacuo
  9. customgiving a yellow oil, 0.70 g, 79%

출처 및 근거

ORD 기록
ord-d52bd4e513cb4a59a20f3a78ffee7fff
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521188

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