Tetrabutylammonium Fluoride → Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-hydroxybutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

HRID 1036631노트

반응식

HRID 1036631 반응식
[Si]([O:8][CH2:9][CH2:10][C@@H:11]([NH:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[C:15]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:14]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>ClCCl>[F:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([NH:27][C@H:11]([CH2:10][CH2:9][OH:8])[CH2:12][N:13]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:14]2)(=[O:30])=[O:29])=[CH:32][CH:33]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86655913methyl [1-((2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(4-fluorophenyl)sulfonyl]amino}butyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

생성물 1

HCID 86655914Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-hydroxybutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate수율 88.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl [1-((2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(4-fluorophenyl)sulfonyl]amino}butyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (1.2 g, 2.2 mmol) in dichloromethane (40 mL) was added 1 M TBAF (4.8 mL, 2.2 equiv.). After a period of 0.5 h the reaction mixture was quenched with 25% aqueous ammonium acetate, the organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified on combiflash (20% ethyl acetate in hexane to 100% ethyl acetate) to provide 849 mg of the title compound.

후처리

  1. customAfter a period of 0.5 h the reaction mixture was quenched with 25% aqueous ammonium acetate
  2. customthe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified on combiflash (20% ethyl acetate in hexane to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-ae248ef9b2d04e1dbe424e31385a62a4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546422B2

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