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

HRID 471245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471245
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-16f18d8e7ff2473ea7baf50cd607e224
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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