Diisopropylethylamine → 5-[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-1,3-oxazolidin-2-one

HRID 1994490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994490
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[O:24][CH3:25])[OH:4].C(N(C(C)C)CC)(C)C.Cl[C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:21]([C:19]1[CH:18]=[CH:17][C:16]([O:24][CH3:25])=[C:15]([C:6]2[CH:7]=[CH:8][C:9]([C:11]([F:13])([F:14])[F:12])=[CH:10][C:5]=2[CH:3]2[O:4][C:36](=[O:38])[NH:1][CH2:2]2)[CH:20]=1)([CH3:23])[CH3:22]

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 667170952-Amino-1-[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]ethanol

Produkt 1

HCID 591351825-[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of 0.44 g of 2-amino-1-[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]ethanol in 15 mL of CH2Cl2 was added 0.241 g of diisopropylethylamine, then 0.185 g of triphosgene. The mixture was stirred at 0° C. for 30 min, and then diluted with 30 mL of EtOAc and 20 mL of saturated NaHCO3. The phases were separated and the organic phase was washed with 20 mL of brine, dried (Na2SO4), and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 40S column, eluting with 1 CV of 5% EtOAc in hexanes, followed by a linear gradient of EtOAc in hexanes from 5 to 100% over 10 CV to provide the title compound. Mass spectrum (ESI) 380.2 (M+1). 1H NMR signals are doubled because of atropoisomerism 1H NMR (500 MHz, CDCl3): δ 7.90, 7.86 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.35 (d, J=8 Hz, 1H), 7.27 (dd, J=2.5 Hz, 8.5 Hz 1H), 7.03 (d, J=2.5 Hz, 0.5H), 6.87-6.93 (m, 1.5H), 5.65, 5.50 (t, J=8 Hz, 1H), 5.23, 5.09 (s, 1H), 3.75 (s, 1.5H), 3.69 (s, 1.5H), 3.68, 3.51 (t, J=9 Hz, 1H), 3.31, 3.19 (t, J=8.5 Hz, 0.5H), 2.90 (septet, J=7 Hz, 1H), 1.25, 1.24 (d, J=7 Hz, 6H).

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed with 20 mL of brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on a Biotage Horizon, 40S column
  6. washeluting with 1 CV of 5% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-87844c4629f74190894a768fe77079ed
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652049B2

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