Trifluoroacetic acid → US9434719, 268 as TFA salt

HRID 57496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57496
C([O:5][C@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C@H:21]([C:23]2[S:27][C:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[N:25][CH:24]=2)[CH3:22])[N:15]=1)[CH3:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]2[S:27][C:23]([C@@H:21]([NH:20][C:16]3[N:15]=[C:14]([N:9]4[C@@H:8]([C@@H:6]([OH:5])[CH3:7])[CH2:12][O:11][C:10]4=[O:13])[CH:19]=[CH:18][N:17]=3)[CH3:22])=[CH:24][N:25]=2)=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 90414586(R)-4-((S)-1-(tert-butoxy)ethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

Produkt 1

HCID 90414838US9434719, 268 as TFA saltAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a round bottom flask containing a stir bar and (R)-4-((S)-1-(tert-butoxy)ethyl)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (82 mg, 0.16 mmol) was added DCM (1 mL) followed by the addition of TFA (1 mL). Resulting reaction mixture allowed to stir 30 min at RT. The volatiles were then removed and the residue neutralized by the addition of a saturated solution of NaHCO3. The aqueous mixture was then extracted with DCM. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated to a brown foam of (R)-3-(2-(((S)-1-(2-(4-chlorophenyl)thiazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((S)-1-hydroxyethyl)oxazolidin-2-one (61 mg, 0.14 mmol, 84% yield) which was used without further purification. LCMS m/z 446.2 (M+H)+, Rt 0.71 min.

Aufarbeitung

  1. additionTo a round bottom flask containing a stir bar
  2. customResulting
  3. customreaction mixture
  4. customThe volatiles were then removed
  5. additionthe residue neutralized by the addition of a saturated solution of NaHCO3
  6. extractionThe aqueous mixture was then extracted with DCM
  7. washwashed with water, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9ea056c571734e198840b8a429991b77
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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