Trifluoroacetic acid → (5-Methylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 1689475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689475
FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:13][CH:12]=[C:11]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[CH:10]=1>C(Cl)Cl>[CH3:8][C:9]1[S:13][CH:12]=[C:11]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[CH:10]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57989109Tert-butyl 4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Produkt 1

HCID 57988956(5-Methylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (2.5 mL) was added to a solution of tert-butyl 4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 104, step a) (0.34 g) in DCM (10 mL) and the resulting mixture was stirred for 45 minutes and allowed to stand overnight. The solvent was evaporated in vacuo. Toluene (3×25 mL) was added and the mixture evaporated in vacuo. The residue was dissolved in methanol (20 mL) and applied to a SCX cartridge pre-wetted with methanol. The cartridge was washed with methanol (40 mL) and eluted with 2M ammonia in methanol solution (20 mL). The eluent was evaporated in vacuo to give the subtitled compound as a colourless oil. Yield 0.25 g.

Aufarbeitung

  1. waitto stand overnight
  2. customThe solvent was evaporated in vacuo
  3. additionToluene (3×25 mL) was added
  4. customthe mixture evaporated in vacuo
  5. dissolutionThe residue was dissolved in methanol (20 mL)
  6. washThe cartridge was washed with methanol (40 mL)
  7. washeluted with 2M ammonia in methanol solution (20 mL)
  8. customThe eluent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b23a193e4557437b908464b3d71565f0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

Notizen zur Reaktion

Wird geladen…