Trifluoroacetic acid → (2S)-2-[2-borono-4-(trifluoromethyl)phenoxy]-propanoic acid

HRID 1694739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694739
C(O)(C(F)(F)F)=O.CC1(C)C(C)(C)[O:12][B:11]([C:16]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:17]=2[O:18][C@@H:19]([CH3:27])[C:20]([O:22]C(C)(C)C)=[O:21])[O:10]1>C(Cl)Cl>[B:11]([C:16]1[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][C:17]=1[O:18][C@@H:19]([CH3:27])[C:20]([OH:22])=[O:21])([OH:12])[OH:10]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866092221,1-Dimethylethyl (2S)-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)phenoxy]propanoate

Produkt 1

HCID 67277101(2S)-2-[2-borono-4-(trifluoromethyl)phenoxy]-propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (10 ml) was added to a solution of the product from step (iii) (4.0 g) in DCM (100 ml) and stirred for 30 min. The TPA was evaporated and the residue dissolved in a mixture of 1M hydrochloric acid (30 ml) and acetonitrile (30 ml) After 1 h the mixture was evaporated to dryness, dissolved in 1M sodium hydroxide, washed with ether and adjusted to pH 2 with concentrated hydrochloric acid. The aqueous was then extracted with ether, washed with brine, dried (MgSO4) and evaporated. Yield 2.0 g. The crude material was carried forward to step (v).

Aufarbeitung

  1. customThe TPA was evaporated
  2. dissolutionthe residue dissolved in a mixture of 1M hydrochloric acid (30 ml) and acetonitrile (30 ml) After 1 h the mixture
  3. customwas evaporated to dryness
  4. dissolutiondissolved in 1M sodium hydroxide
  5. washwashed with ether
  6. extractionThe aqueous was then extracted with ether
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0df6858cd1ce47ed90df9e3a269f3b6c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158820B2

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