Tetrabutylammonium Fluoride → (9-((5-(2-Hydroxyethyl)thiophen-3-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 471307ノート

反応式

HRID 471307 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][C:29]1[S:33][CH:32]=[C:31]([CH2:34][N:35]2[CH2:55][CH2:54][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[N:47]=[C:48]([CH:51]([CH3:53])[CH3:52])[S:49][CH:50]=4)=[O:45])[CH2:39]3)[CH2:37][CH2:36]2)[CH:30]=1)(C(C)(C)C)(C)C>O1CCCC1>[OH:26][CH2:27][CH2:28][C:29]1[S:33][CH:32]=[C:31]([CH2:34][N:35]2[CH2:55][CH2:54][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[N:47]=[C:48]([CH:51]([CH3:52])[CH3:53])[S:49][CH:50]=4)=[O:45])[CH2:39]3)[CH2:37][CH2:36]2)[CH:30]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 57988978(9-((5-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophen-3-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

生成物 1

HCID 57989163(9-((5-(2-Hydroxyethyl)thiophen-3-yl)methyl)-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

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 2.1 mL) was added to a solution of (9-((5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-3-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 278, step d) (0.80 g) in tetrahydrofuran (10 mL). After 2 h, the solution was evaporated in vacuo and the residue partitioned between saturated sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×50 mL). The combined organic solutions were washed with brine (50 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography, eluting with 20:1 ethyl acetate:triethylamine. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a gum. Yield 0.61 g.

後処理

  1. customthe solution was evaporated in vacuo
  2. customthe residue partitioned between saturated sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic solutions were washed with brine (50 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 20:1 ethyl acetate
  11. additionThe fractions containing product
  12. customevaporated in vacuo

出典と根拠

ORDレコード
ord-02feb54e2d61468f8843592a64a3bca3
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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