Trifluoroacetic acid → 2-(5-((4-(2-Methylbenzo[d]thiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

HRID 1689325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689325
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH2:31][N:32]2[CH2:54][CH2:53][C:35]3([O:40][CH2:39][CH2:38][N:37]([C:41]([C:43]4[CH:44]=[CH:45][C:46]5[S:50][C:49]([CH3:51])=[N:48][C:47]=5[CH:52]=4)=[O:42])[CH2:36]3)[CH2:34][CH2:33]2)[S:29][CH:30]=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>[CH3:51][C:49]1[S:50][C:46]2[CH:45]=[CH:44][C:43]([C:41]([N:37]3[CH2:36][C:35]4([CH2:53][CH2:54][N:32]([CH2:31][C:28]5[S:29][CH:30]=[C:26]([CH2:25][CH:24]=[O:23])[CH:27]=5)[CH2:33][CH2:34]4)[O:40][CH2:39][CH2:38]3)=[O:42])=[CH:52][C:47]=2[N:48]=1

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989243(9-((4-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone

Produkt 1

HCID 579890032-(5-((4-(2-Methylbenzo[d]thiazole-5-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 (0.27 g) was added to stirred solution of (9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylbenzo[d]thiazol-5-yl)methanone (example 49, step b) (0.20 g) and trifluoroacetic acid (0.033 mL) in DCM (5 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 solution was dried over sodium sulphate, filtered, and evaporated in vacuo. Yield 0.2 g. Used directly in the next step.

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 solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1b37d24de5e74971a619e39395b9335d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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