Sodium Hydroxide → Tegoprazan

HRID 2239304ノート

反応式

HRID 2239304 の反応式
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([O:13][C:14]1[C:22]3[N:21]=[C:20]([CH3:23])[N:19](S(C4C=CC(C)=CC=4)(=O)=O)[C:18]=3[CH:17]=[C:16]([C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH:15]=1)[CH2:5][CH2:6][O:7]2.[OH-].[Na+]>O1CCCC1.CC(O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([O:13][C:14]1[C:22]3[N:21]=[C:20]([CH3:23])[NH:19][C:18]=3[CH:17]=[C:16]([C:34]([N:36]([CH3:37])[CH3:38])=[O:35])[CH:15]=1)[CH2:5][CH2:6][O:7]2

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 68574320N-tosyl Tegoprazan

生成物 1

HCID 23582846Tegoprazan収率 87.8%

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (−)-4-[((4S)-5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N,N,2-trimethyl-1-[(4-methylphenyl)-sulfonyl]-1H-benzimidazole-6-carboxamide (24.2 g, 44.7 mmol, STEP 9) in tetrahydrofuran (65 mL) and 2-propanol (220 mL) was added 2M sodium hydroxide aqueous solution (220 mL, 440 mmol) at room temperature. After stirring at room temperature for 4 hours, the mixture was diluted with ethyl acetate (1.20 L) and washed with saturated ammonium chloride aqueous solution (500 mL). The organic solution was dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on amino gel (ethyl acetate:methanol gradient elution from 50:1 to 20:1) to afford the title compound as a white solid (15.2 g, 87%, >99% ee).

後処理

  1. washwashed with saturated ammonium chloride aqueous solution (500 mL)
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by column chromatography on amino gel (ethyl acetate:methanol gradient elution from 50:1 to 20:1)

出典と根拠

ORDレコード
ord-ef759a7d7fb240c2a54aeebe9b89d931
出典データセット
uspto-grants-2010_05
特許番号
US07723321B2

反応ノート

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