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

HRID 132462노트

반응식

HRID 132462 반응식
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

참가 물질

4

반응물 2

HCID 164537Methanol, magnesium salt (2:1)HCID 178471822HCID 178471822, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-54eca71df4ec46e9ad77b666336deb42
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

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