Tetrabutylammonium Fluoride → HCID 10359151, 화합물

HRID 1271863노트

반응식

HRID 1271863 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:25][C:19]=2[CH:18]=1)=[O:16])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][OH:29])=[CH:25][C:19]=2[CH:18]=1)=[O:16]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 69489781HCID 69489781, 화합물

생성물 1

HCID 10359151HCID 10359151, 화합물수율 52%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 55 mg (0.100 mmol) [2-({5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzo[b]thiophene-2-carbonyl}-amino)-phenyl]-carbamic acid tert-butyl ester (40) in 5 ml tetrahydrofurane was added 38 mg (0.120 mmol) tetra-n-butylammonium fluoride. The reaction mixture was stirred at room temperature for 1 h and poured into brine. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed brine and dried over sodium sulfate. The solvent was evaporated and the residue of (2-{[5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester was dissolved in 1.0 ml trifluoroacetic acid. The reaction mixture was stirred for 45 min at room temperature and then added to an aqueous solution of sodium bicarbonate. After extraction with ethyl acetate and removal of the solvent the residue was recrystallized from ethyl acetate/diethyl ether to yield 17 mg (0.052 mmol) of 5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carboxylic acid (2-amino-phenyl)-amide (39) as a white solid, mp. 215–216° C.

후처리

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined organic phases were washed brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. dissolutionthe residue of (2-{[5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester was dissolved in 1.0 ml trifluoroacetic acid
  6. stirringThe reaction mixture was stirred for 45 min at room temperature
  7. additionadded to an aqueous solution of sodium bicarbonate
  8. extractionAfter extraction
  9. customwith ethyl acetate and removal of the solvent the residue
  10. customwas recrystallized from ethyl acetate/diethyl ether

출처 및 근거

ORD 기록
ord-d9dde0876ffc47398e9fc6472d29a1eb
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208491B2

반응 노트

불러오는 중…