Water → (S)-2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinic acid

HRID 132455ノート

反応式

HRID 132455 の反応式
[Br:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][O:12][C:13](=[O:21])[C@H:14]([CH2:16][C:17]([O:19]C)=[O:18])[CH2:15][C:4]=2[CH:3]=1.[OH2:22].O.[OH-].[Li+]>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][C@@H:14]([CH2:16][C:17]([OH:19])=[O:18])[C:13]([OH:12])=[O:21])[C:5]([CH2:11][OH:22])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

参加物

6

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2 回HCID 59732087(S)-methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate

生成物 1

HCID 59732086(S)-2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinic acid収率 73%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(S)-Methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate (135 mg, 0.368 mmol) was dissolved in a mixture of tetrahydrofuran (4.0 mL) and methanol (4.0 mL). Water (4.0 mL) was added to the mixture followed by lithium hydroxide hydrate (31.5 mg, 0.751 mmol). Reaction stirred at room temperature for 5 hours. Another 30 mg of lithium hydroxide hydrate was added to the mixture. Reaction stirred at room temperature for 18 hours. Reaction was quenched with 1.6 mL 1N hydrochloric acid. Organic solvents were removed from the mixture by roto-vap. Material was extracted from the remaining aqueous twice with ethyl acetate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 73% yield. MS (M−H)−=355.2, 357.1.

後処理

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 18 hours
  4. customReaction
  5. customwas quenched with 1.6 mL 1N hydrochloric acid
  6. customOrganic solvents were removed from the mixture by roto-vap
  7. extractionMaterial was extracted from the remaining aqueous twice with ethyl acetate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-861e42cad64a40a5ba91fbb649fd6c36
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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