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

HRID 471098

Reaktionsgleichung

Reaktionsgleichung von HRID 471098
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][C:29]1[CH:30]=[C:31]([CH2:34][N:35]2[CH2:57][CH2:56][C:38]3([O:43][C:42]([F:45])([F:44])[CH2:41][N:40]([C:46]([C:48]4[N:49]=[C:50]([CH:53]([CH3:55])[CH3:54])[S:51][CH:52]=4)=[O:47])[CH2:39]3)[CH2:37][CH2:36]2)[S:32][CH:33]=1)(C(C)(C)C)(C)C>C1COCC1>[F:45][C:42]1([F:44])[CH2:41][N:40]([C:46]([C:48]2[N:49]=[C:50]([CH:53]([CH3:54])[CH3:55])[S:51][CH:52]=2)=[O:47])[CH2:39][C:38]2([CH2:56][CH2:57][N:35]([CH2:34][C:31]3[S:32][CH:33]=[C:29]([CH2:28][CH2:27][OH:26])[CH:30]=3)[CH2:36][CH2:37]2)[O:43]1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 57989002(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Produkt 1

HCID 57989282(2,2-Difluoro-9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TBAF (1M in THF, 1.5 mL) was added to a stirred solution of (9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 51, step a) (0.30 g) in THF (3 mL). After 1 h, the reaction was evaporated in vacuo to a gum. Purification by silica gel chromatography eluting with ethyl acetate:triethylamine, 20:1 gave the subtitled compound as a gum. Yield 0.2 g.

Aufarbeitung

  1. customthe reaction was evaporated in vacuo to a gum
  2. customPurification by silica gel chromatography
  3. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4908e41a07944784ba0b54ff6ca9ff6e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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