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Trifluoroacetic acid → (2-Ethylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

HRID 1255314
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1255314
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([C:10]1[S:11][CH:12]=[C:13]([C:15]([N:17]2[CH2:22][C:21]3([CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[O:20][CH2:19][CH2:18]2)=[O:16])[N:14]=1)[CH3:9]>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([C:10]1[S:11][CH:12]=[C:13]([C:15]([N:17]2[CH2:22][C:21]3([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[O:20][CH2:19][CH2:18]2)=[O:16])[N:14]=1)[CH3:9]
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Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58168458Tert-butyl 4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Produkt 1

HCID 66964094(2-Ethylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (20 mL) was added to a solution of tert-butyl 4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate [Example 26, step a] (24 g) in dichloromethane (100 mL) and the mixture stirred at ambient temperature for 18 hours. The reaction mixture was diluted with toluene (50 mL) and concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL), TFA (50 mL) was added and the mixture was stirred for 4 hours. The mixture was diluted with toluene (50 mL), concentrated in vacuo, the residue triturated with ether and the precipitated solid collected by filtration and dried to afford the subtitled compound as a white solid. Yield 28 g.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. additionTFA (50 mL) was added
  4. stirringthe mixture was stirred for 4 hours
  5. additionThe mixture was diluted with toluene (50 mL)
  6. concentrationconcentrated in vacuo
  7. customthe residue triturated with ether
  8. filtrationthe precipitated solid collected by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3e553ab8c2dd4696a48ded35e5d82b60
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08455483B2

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