Methanol, magnesium salt (2:1) → (S)-dimethyl 2-((3,7-dichloro-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

HRID 2378925ノート

反応式

HRID 2378925 の反応式
C([O:4][CH2:5][C:6]1[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH2:26]C)=[O:24])[C:17]([O:19][CH2:20]C)=[O:18])=[CH:13][C:12]([Cl:28])=[C:11]2[C:7]=1[C:8]([Cl:29])=[N:9][NH:10]2)(=O)C.C[O-].[Mg+2].C[O-]>CO>[Cl:29][C:8]1[C:7]2[C:11](=[C:12]([Cl:28])[CH:13]=[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:17]([O:19][CH3:20])=[O:18])[C:6]=2[CH2:5][OH:4])[NH:10][N:9]=1

参加物

4

反応物 2

HCID 164537Methanol, magnesium salt (2:1)HCID 178471822HCID 178471822、化合物

生成物 1

HCID 178500726(S)-dimethyl 2-((3,7-dichloro-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

(S)-Diethyl 2-((4-(acetoxymethyl)-3,7-dichloro-1H-indazol-5-yl)methyl)succinate (1.30 g, 2.92 mmol) was dissolved in methanol (45 mL). 6-10% Magnesium methoxide in methanol (8.4 mL, 6.35 mmol) was added to the mixture. Reaction stirred at room temperature for 16 hours. Reaction was quenched with 14 mL 1N hydrochloric acid. Methanol was removed from the mixture by roto-vap. Residue was treated with aqueous sodium bicarbonate. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. The combined organic phases were washed with water and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as dark amber oil in 91% yield. MS (M−H)−=373.0, 375.0.

後処理

  1. customReaction
  2. customReaction
  3. customwas quenched with 14 mL 1N hydrochloric acid
  4. customMethanol was removed from the mixture by roto-vap
  5. additionResidue was treated with aqueous sodium bicarbonate
  6. extractionMaterial was extracted twice with ethyl acetate
  7. washThe combined organic phases were washed with water
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-306bdca1d0bd40638464931dfc408001
出典データセット
uspto-grants-2008_12
特許番号
US07470680B2

反応ノート

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