p-Toluenesulfonic acid monohydrate → (S)-methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate

HRID 2378917노트

반응식

HRID 2378917 반응식
Br[C:2]1[C:10]2[C:5](=[C:6]([Br:24])[CH:7]=[C:8]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17][CH3:18])=[O:16])[C:9]=2CO)[NH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:24][C:6]1[C:5]2[NH:4][N:3]=[CH:2][C:10]=2[C:9]2[CH2:18][O:17][C:15](=[O:16])[C@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:13][C:8]=2[CH:7]=1

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178500724(S)-dimethyl 2-((3,7-dibromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

생성물 1

HCID 59732087(S)-methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate수율 42%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

(S)-Dimethyl 2-((3,7-dibromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate (440 mg, 1.065 mmol) was dissolved in toluene (30 mL). p-Toluenesulfonic acid monohydrate (28 mg, 0.147 mmol) was added to the mixture. Reaction was warmed to reflux and held for 18 hours with stirring. Mixture was cooled to room temperature and then diluted with ethyl acetate. Material was washed with aqueous sodium bicarbonate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as amber oil in 42% yield. MS (M+H)+=367.2, 369.2.

후처리

  1. customReaction
  2. temperaturewas warmed
  3. temperatureto reflux
  4. washMaterial was washed with aqueous sodium bicarbonate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. washSilica gel chromatography eluting ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-7925a856f01f4fdd910d3f4e2d3de783
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470680B2

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