2-(Benzenesulfonyl)-3-phenyloxaziridine → 9-hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11034

반응식

HRID 11034 반응식
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[S:21][CH3:22])[C:7]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:35])C=CC=CC=1>C1COCC1>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[S:21]([CH3:22])=[O:35])[C:7]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 99766729-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 118431439-hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

A mixture of the 9-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (508) (34.5 mg, 0.092 mmol), prepared according to example 25, and 2-phenylsulfonyl-3-phenyloxaziridine (Davis reagent) (26.5 mg, 0.102 mmol) in THF (10 mL) was stirred at 20° C. for 2.5 h, then adsorbed directly onto silica gel and chromatographed. Elution with 0–3% MeOH/CH2Cl2 then 3–4% MeOH/CH2Cl2 gave (after crystallisation from THF/CH2Cl2/pentane) the 9-Hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (510) (I; Ar=2-(methylsulfinyl)phenyl) in a 86% yield as a yellow solid; mp 321–323° C. 1H NMR [(CD3)2SO] δ 11.86, 11.85 (2br s, 1H), 11.09 (br s, 1H), 9.30 (br s, 1H), 8.32 (d, J=2.4 Hz, 1H), 8.04, 7.97 (2d, J=7.6 Hz, 1H), 7.74 (t, J=7.6 Hz, 1H), 7.65, 7.62 (2t, J=7.4 Hz, 1H), 7.62, 7.54 (2s, 1H), 7.47 (d, J=9.1 Hz, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.09 (dd, J=8.7, 2.5 Hz, 1H), 2.43, 2.31 (2s, 3H). Found: C, 64.60; H, 3.88; N, 6.87. C21H14N2O4S requires C, 64.61; H, 3.61; N, 7.18.

후처리

  1. customprepared
  2. customchromatographed
  3. washElution with 0–3% MeOH/CH2Cl2
  4. custom3–4% MeOH/CH2Cl2 gave
  5. custom(after crystallisation from THF/CH2Cl2/pentane) the 9-Hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (510) (I; Ar=2-(methylsulfinyl)phenyl) in a 86% yield as a yellow solid

출처 및 근거

ORD 기록
ord-1ca742a96a8a47d7846b28718434176e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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