N-Iodosuccinimide → Compound 3

HRID 1247479

Reaktionsgleichung

Reaktionsgleichung von HRID 1247479
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.[I:16]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][C:7]=1[I:16]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 2071332-Oxazolidinone, 3-(m-fluorophenyl)-5-hydroxymethyl-

Produkt 1

HCID 20788885Compound 3Ausbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of alcohol 92 (10.74 g, 50.9 mmol) in trifluoroacetic acid (TFA, 50 mL) was treated with N-iodosuccinimide (12.03 g, 53.45 mmol, 1.05 equiv) at 25° C. and stirred for 2 h. When TLC and HPLC/MS showed the reaction was complete, the reaction mixture was concentrated in vacuo. The residue was then treated with H2O (100 mL) and 20% EtOAc/hexane (100 mL) at 25° C., and the resulting mixture was stirred at 25° C. for 30 min before being cooled to 0–5° C. for 2 h. The white solids were collected by filtration, washed with H2O (2×25 mL) and 20% EtOAc/hexane (2×25 mL), and dried in vacuo to afford the desired (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-oxazolidin-2-one (iodo-alcohol 93, 15; 1 g, 88% yield) as an off-white powder. This product was directly used in subsequent reactions without further purification. 1H NMR (300 MHz, DMSO-d6) δ 3.58 (dd, 1H, J=4.2, 12.6 Hz), 3.67 (dd, 1H, J=3.0, 12.6 Hz), 3.67 (dd, 1H, J=6.3, 9.0 Hz), 4.07(t, 1H, J=9.0 Hz), 4.72 (m, 1H), 5.21 (br. s, 1H, OH), 7.22 (dd, 1H, J=2.4, 8.4 Hz), 7.58 (dd, 1H, J=2.4, 11.1 Hz), 7.81 (dd, 11H, J=7.8, 8.7 Hz). C10H9FINO3, LCMS (EI) m/e 338 (M++H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was then treated with H2O (100 mL) and 20% EtOAc/hexane (100 mL) at 25° C.
  3. stirringthe resulting mixture was stirred at 25° C. for 30 min
  4. temperaturebefore being cooled to 0–5° C. for 2 h
  5. filtrationThe white solids were collected by filtration
  6. washwashed with H2O (2×25 mL) and 20% EtOAc/hexane (2×25 mL)
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d86eabf4f28a4c6b886eece54bc59916
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129259B2

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