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 471307노트

반응식

HRID 471307 반응식
[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

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02feb54e2d61468f8843592a64a3bca3
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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