Tetrabutylammonium Fluoride → HCID 136016222, 화합물

HRID 2078719노트

반응식

HRID 2078719 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C)C)[CH:15]=2)[CH:10]=[C:9]1[C:25]1[C:26]2[S:39][C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:37][C:27]=2[N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[C:9]1[C:25]1[C:26]2[S:39][C:38]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:37][C:27]=2[N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:29]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 57637385HCID 57637385, 화합물2회

생성물 1

HCID 136016222HCID 136016222, 화합물수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-(1-tert-butoxycarbonyl-5-phenyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester [2.44 g, 3.78 mmol, Intermediate (48)] in tetrahydrofuran (25 mL) at 0° C. was added tetrabutylammonium fluoride (4.20 mL of a 1M THF solution, 4.20 mmol) in one portion with stirring. After 40 minutes, the reaction was partitioned between ethyl acetate (75 mL) and 10% aqueous ammonium chloride (50 mL) and the layers separated. The organics were washed with water (50 mL) and brine (50 mL) successively, dried over magnesium sulfate, and the solvent removed under reduced pressure to give an amber foam. The crude product was chromatographed on silica, eluting with 10% ethyl acetate/dichloromethane, to yield 2-(1-tert-butoxycarbonyl-5-phenyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-hydroxy-indole-1-carboxylic acid tert-butyl ester [1.99 g, 99%, Intermediate (49)] as a tan foam. TLC Rf 0.31 (silica, 10% ethyl acetate/dichloromethane); LC/MS: 532.2 (M+H), RT=4.31 minutes; 1H NMR [300 Mhz, (CD3)2SO]: δ 9.73 (s, 1H), 7.84-7.81 (m, 2H), 7.76 (s, 1H), 7.61 (d, J=2 Hz, 1H), 7.56-7.44 (m, 4H), 7.07 (s, 1H), 6.84 (dd, J=2, 8 Hz, 1H), 1.71 (s, 9H), 1.40 (s, 9H).

후처리

  1. customthe reaction was partitioned between ethyl acetate (75 mL) and 10% aqueous ammonium chloride (50 mL)
  2. customthe layers separated
  3. washThe organics were washed with water (50 mL) and brine (50 mL) successively
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customto give an amber foam
  7. customThe crude product was chromatographed on silica
  8. washeluting with 10% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-855ae489a02e471ca427756915c1fe58
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928231B2

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