Tetrabutylammonium Fluoride → (9-(2-Fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 446430

反応式

HRID 446430 の反応式
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][C:29]1[C:30]([F:57])=[C:31]([CH:54]=[CH:55][CH:56]=1)[CH2:32][N:33]1[CH2:53][CH2:52][C:36]2([O:41][CH2:40][CH2:39][N:38]([C:42]([C:44]3[N:45]=[C:46]([CH:49]([CH3:51])[CH3:50])[S:47][CH:48]=3)=[O:43])[CH2:37]2)[CH2:35][CH2:34]1)(C(C)(C)C)(C)C>C1COCC1>[F:57][C:30]1[C:29]([CH2:28][CH2:27][OH:26])=[CH:56][CH:55]=[CH:54][C:31]=1[CH2:32][N:33]1[CH2:34][CH2:35][C:36]2([O:41][CH2:40][CH2:39][N:38]([C:42]([C:44]3[N:45]=[C:46]([CH:49]([CH3:51])[CH3:50])[S:47][CH:48]=3)=[O:43])[CH2:37]2)[CH2:52][CH2:53]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 58168600(9-(3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

生成物 1

HCID 57989273(9-(2-Fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

TBAF (1M in THF, 13.9 mL) was added to a solution of (9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone [Example 7, step a] (5.35 g) in THF (50 mL) and the resulting mixture was stirred for 1 h. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The layers were separated and the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with brine (100 mL), dried over sodium sulphate, filtered and evaporated. The crude material was purified by flash silica chromatography, elution gradient 4:1 isohexane:ethyl acetate to 100% ethyl acetate to give the subtitled compound as a clear oil. Yield 3.90 g.

後処理

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic phases were washed with brine (100 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude material was purified by flash silica chromatography, elution gradient 4:1 isohexane

出典と根拠

ORDレコード
ord-1a7726104f1a4b60a29d995df07f4335
出典データセット
uspto-grants-2013_07
特許番号
US08476265B2

関連ノート

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