Sodium Hydroxide → Tegoprazan

HRID 2239304노트

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HRID 2239304 반응식
[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

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 68574320N-tosyl Tegoprazan

생성물 1

HCID 23582846Tegoprazan수율 87.8%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ef759a7d7fb240c2a54aeebe9b89d931
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723321B2

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