Trifluoroacetic acid → (5S)-3-[3-fluoro-4-[4-(hydroxymethyl)imidazol-1-yl]phenyl]-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one

HRID 8148

Reaktionsgleichung

Reaktionsgleichung von HRID 8148
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]([C:28]4[CH:32]=[CH:31][O:30][N:29]=4)C(OC(C)(C)C)=O)[O:16][C:15]3=[O:33])=[CH:10][C:9]=2[F:34])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[O:30]1[CH:31]=[CH:32][C:28]([NH:20][CH2:19][C@@H:17]2[O:16][C:15](=[O:33])[N:14]([C:11]3[CH:12]=[CH:13][C:8]([N:6]4[CH:7]=[C:3]([CH2:2][OH:1])[N:4]=[CH:5]4)=[C:9]([F:34])[CH:10]=3)[CH2:18]2)=[N:29]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 539752563-(4-(4-Hydroxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

Produkt 1

HCID 497419(5S)-3-[3-fluoro-4-[4-(hydroxymethyl)imidazol-1-yl]phenyl]-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-oneAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(4-(4-Hydroxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (360 mg, 0.76 mM) was dissolved in dichloromethane (10 ml) and treated with trifluoroacetic acid (10 ml). After stirring for 30 minutes solvent was evaporated, the residue repeatedly evaporated to dryness with dichloromethane (3×10 ml), and the resulting gum dissolved in water (10 ml). The solution was made basic with concentrated aqueous ammonia, and the resulting precipitate filtered, washed with water and dried to give title product (190 mg).

Aufarbeitung

  1. customwas evaporated
  2. customthe residue repeatedly evaporated to dryness with dichloromethane (3×10 ml)
  3. dissolutionthe resulting gum dissolved in water (10 ml)
  4. filtrationthe resulting precipitate filtered
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a0a6c4dccdde4393b6c140e0b62c2cd2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087629B2

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