Toluene → (2-Phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 471262

Reaktionsgleichung

Reaktionsgleichung von HRID 471262
FC(F)(F)C(O)=O.[C:8]1([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:26][C:25]4([CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[O:24][CH2:23][CH2:22]3)=[O:20])[N:18]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[C:8]1([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:26][C:25]4([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[O:24][CH2:23][CH2:22]3)=[O:20])[N:18]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989358tert-Butyl 4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Produkt 1

HCID 57989130(2-Phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (3.8 mL) was added to a solution of tert-butyl 4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 112, step a) (0.85 mg) in DCM (15.2 mL). The resulting mixture was stirred at RT for 1 h. Toluene (30 mL) was added and the mixture was evaporated in vacuo. The yellow residue was dissolved in MeOH and applied to a SCX cartridge pre-wetted with MeOH. The cartridge was washed with MeOH and eluted with 2M ammonia in MeOH. The eluent was evaporated in vacuo to give the subtitled compound as a brown oil. Yield 0.629 g.

Aufarbeitung

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe yellow residue was dissolved in MeOH
  3. washThe cartridge was washed with MeOH
  4. washeluted with 2M ammonia in MeOH
  5. customThe eluent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe9c62f9d4b84c97bddd227ef6a9e67e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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