Triethylamine → 2-(Trimethylsilyl)ethyl 2-phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethylcarbamate

HRID 238795

Reaktionsgleichung

Reaktionsgleichung von HRID 238795
[C:1]1([CH2:7][C:8]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:36](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:58][Si:59]([CH:62](O)[CH3:63])([CH3:61])[CH3:60].CC[O:67][C:68](C)=[O:69]>O1CCOCC1>[C:1]1([CH2:7][C:8]([NH:36][C:68](=[O:69])[O:67][CH2:63][CH2:62][Si:59]([CH3:61])([CH3:60])[CH3:58])([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:32])([F:33])[F:31])[CH:24]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 124478981-(Trimethylsilyl)ethanolHCID 594595163-Phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanoic acid

Produkt 1

HCID 235820952-(Trimethylsilyl)ethyl 2-phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethylcarbamateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)propanoic acid (0.055 g, 0.117 mmol) in 1,4-dioxane (2 mL) was added triethylamine (0.014 g, 20 μL, 0.14 mmol), 4 Å molecular sieves (0.05 g), diphenylphosphoryl azide (0.040 g, 31 μL, 0.14 mmol) and trimethylsilylethanol (0.042 g, 50 μL, 0.35 mmol). The reaction mixture was stirred for 1 h at rt, then heated at 75° C. for 1.5 h. The cooled reaction mixture was diluted with EtOAc and filtered through celite. The filtrate was concentrated under reduced pressure and purified by ISCO silica gel chromatography using a gradient of 0-20% EtOAc/hexane as eluent to yield 2-(trimethylsilyl)ethyl 2-phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethylcarbamate (Example 282) as a colorless band (0.037 g, 54% yield). HPLC: RT=4.828 min (Phenomenex Luna C18 5μ column 4.6×50 mm, eluting with 10-90% MeOH/H2O containing 0.1% PPA over a 4 minute gradient, monitoring at 220 nm). No molecular ion was obtained. 1H NMR (400 MHz, CDCl3): 7.32 (t, J=8.1 Hz, 2H), 7.18-7.11 (m, 7H), 6.99 (s, 2H), 6.65 (d, J=7.1 Hz, 2H), 5.35 (s, 1H), 4.08 (t, J=8.8 Hz, 2H), 3.78 (s, 2H), 0.88 (br, 2H), 0.00 (s, 9H).

Aufarbeitung

  1. temperatureheated at 75° C. for 1.5 h
  2. customThe cooled reaction mixture
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by ISCO silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b72548c734ed4a2c8d6272c7263237a0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642576B2

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