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

HRID 471198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471198
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([C:25]1[S:29][CH:28]=[C:27]([C:30]([N:32]2[CH2:37][C:36]3([CH2:42][CH2:41][N:40]([CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50][CH2:51][OH:52])[CH:45]=4)[CH2:39][CH2:38]3)[O:35][CH2:34][CH2:33]2)=[O:31])[CH:26]=1)[CH3:24].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>[CH2:23]([C:25]1[S:29][CH:28]=[C:27]([C:30]([N:32]2[CH2:37][C:36]3([CH2:42][CH2:41][N:40]([CH2:43][C:44]4[CH:45]=[C:46]([CH2:50][CH:51]=[O:52])[CH:47]=[CH:48][CH:49]=4)[CH2:39][CH2:38]3)[O:35][CH2:34][CH2:33]2)=[O:31])[CH:26]=1)[CH3:24]

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989056(5-Ethylthiophen-3-yl)(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Produkt 1

HCID 579893622-(3-((4-(5-Ethylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dess-Martin periodinane (0.232 g) was added to a stirred solution of (5-ethylthiophen-3-yl)(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 86, step a) (0.180 g) and trifluoroacetic acid (0.042 mL) in DCM (5 mL). After 1 h, ethyl acetate (30 mL) was added followed by a mixture of saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL). The reaction mixture was shaken well and separated. The ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine. Acetic acid (0.08 mL) was added, the solution was dried over sodium sulphate, filtered and evaporated in vacuo (bath temperature ˜30° C.) to give the subtitled compound as a gum. Yield 0.17 g. Used directly.

Aufarbeitung

  1. customseparated
  2. washThe ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine
  3. additionAcetic acid (0.08 mL) was added
  4. dry with materialthe solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo (bath temperature ˜30° C.)

Quellen und Nachweise

ORD-Eintrag
ord-5850ea5bffd443e593720dbd6bafcca2
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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