Trifluoroacetic acid → 2-(5-((2,2-Difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

HRID 1689329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689329
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1([F:54])[CH2:29][N:28]([C:30]([C:32]2[N:33]=[C:34]([CH:37]([CH3:39])[CH3:38])[S:35][CH:36]=2)=[O:31])[CH2:27][C:26]2([CH2:44][CH2:43][N:42]([CH2:45][C:46]3[S:47][CH:48]=[C:49]([CH2:51][CH2:52][OH:53])[CH:50]=3)[CH2:41][CH2:40]2)[O:25]1.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:54][C:24]1([F:23])[CH2:29][N:28]([C:30]([C:32]2[N:33]=[C:34]([CH:37]([CH3:38])[CH3:39])[S:35][CH:36]=2)=[O:31])[CH2:27][C:26]2([CH2:44][CH2:43][N:42]([CH2:45][C:46]3[S:47][CH:48]=[C:49]([CH2:51][CH:52]=[O:53])[CH:50]=3)[CH2:41][CH2:40]2)[O:25]1

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 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

Produkt 1

HCID 579890332-(5-((2,2-Difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dess-Martin periodinane (0.20 g) was added to stirred solution of (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 (example 51, step b) (0.15 g) and trifluoroacetic acid (0.031 mL) in DCM (4 mL). After 40 min, the reaction mixture was treated with aqueous saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (30 mL). The mixture was extracted twice with ethyl acetate, the combined organics were washed with saturated sodium bicarbonate solution, acetic acid (0.08 mL) was added, then the solvent was dried over sodium sulphate, filtered, and evaporated in vacuo. Yield 0.19 g. Used directly.

Aufarbeitung

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. washthe combined organics were washed with saturated sodium bicarbonate solution, acetic acid (0.08 mL)
  3. additionwas added
  4. dry with materialthe solvent was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fc843f5c80ee44c7bc675fa947acbe32
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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