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

HRID 1036631ノート

反応式

HRID 1036631 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ae248ef9b2d04e1dbe424e31385a62a4
出典データセット
uspto-grants-2013_10
特許番号
US08546422B2

反応ノート

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