Trifluoroacetic acid → 2-(2,6-Difluoro-3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 1689311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689311
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:36]([CH2:37][CH2:38][OH:39])=[C:35]([F:40])[CH:34]=[CH:33][C:10]=1[CH2:11][N:12]1[CH2:32][CH2:31][C:15]2([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]3[N:24]=[C:25]([CH:28]([CH3:30])[CH3:29])[S:26][CH:27]=3)=[O:22])[CH2:16]2)[CH2:14][CH2:13]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:8][C:9]1[C:10]([CH2:11][N:12]2[CH2:32][CH2:31][C:15]3([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]4[N:24]=[C:25]([CH:28]([CH3:30])[CH3:29])[S:26][CH:27]=4)=[O:22])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:33][CH:34]=[C:35]([F:40])[C:36]=1[CH2:37][CH:38]=[O:39]

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57988951(9-(2,4-Difluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Produkt 1

HCID 579893052-(2,6-Difluoro-3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

TFA (0.11 mL) was added to a solution of (9-(2,4-difluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 45, step c) (0.7 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.93 g) was then added and the mixture stirred at RT for 45 min. Saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (20 mL) was then added and the mixture stirred for 10 min. The aqueous layer was separated and extracted with ethyl acetate (20 mL). The combined organics were washed with brine, acidified with a few drops of acetic acid, the mixture dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a clear gum.

Aufarbeitung

  1. stirringthe mixture stirred at RT for 45 min
  2. stirringthe mixture stirred for 10 min
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (20 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialthe mixture dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6fe177db68ac4ef4b1c57f9c1d4009d6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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