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 132454ノート

反応式

HRID 132454 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-324c5f78140841f7917e552776197a67
出典データセット
uspto-grants-2008_06
特許番号
US07384931B2

反応ノート

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