Trifluoroacetic acid → 3-Fluoro-5-[[4-[(2-methyl-4-thiazolyl)carbonyl]-1-oxa-4,9-diazaspiro[5.5]undec-9-yl]methyl]benzeneacetaldehyde

HRID 1689238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689238
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([CH2:35][CH2:36][OH:37])[CH:34]=1)[CH2:12][N:13]1[CH2:31][CH2:30][C:16]2([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]3[N:25]=[C:26]([CH3:29])[S:27][CH:28]=3)=[O:23])[CH2:17]2)[CH2:15][CH2:14]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[CH:34]=[C:33]([CH2:35][CH:36]=[O:37])[CH:32]=[C:11]([CH2:12][N:13]2[CH2:31][CH2:30][C:16]3([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]4[N:25]=[C:26]([CH3:29])[S:27][CH:28]=4)=[O:23])[CH2:17]3)[CH2:15][CH2:14]2)[CH:10]=1

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 46240300HCID 46240300, Verbindung

Produkt 1

HCID 579893163-Fluoro-5-[[4-[(2-methyl-4-thiazolyl)carbonyl]-1-oxa-4,9-diazaspiro[5.5]undec-9-yl]methyl]benzeneacetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

TFA (0.08 mL) was added to a solution of (9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 19, step b) (0.46 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.68 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) were then added and the mixture stirred for 10 min. The aqueous phase was separated and extracted with ethyl acetate (20 mL). The combined organic solutions were washed with brine, acidified with acetic acid (0.1 mL), dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a yellow gum. Yield 0.4 g.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-60324889b3b64bfd8bdfe72816c2da47
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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