Pentafluorophenyl Trifluoroacetate → 3-[(tert-Butyl)oxycarbonyl]propyl 2,3,4,5,6-pentafluorophenyl butane-1,4-dioate

HRID 2356301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356301
[C:1]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:14])[CH2:2]CC(OCC1C=CC=CC=1)=O.F[C:27](F)(F)[C:28]([O:30][C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41])=[O:29]>C1COCC1.[Pd]>[C:1]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:14])[CH2:2][CH2:27][C:28]([O:30][C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41])=[O:29]

Komponenten

5

Edukt 2

HCID 4327891Pentafluorophenyl TrifluoroacetateHCID 597306963-[(tert-Butyl)oxycarbonyl]propyl phenylmethyl butane-1,4-dioate

Produkt 1

HCID 597306583-[(tert-Butyl)oxycarbonyl]propyl 2,3,4,5,6-pentafluorophenyl butane-1,4-dioateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Compound 3 (2.0 g, 5.7 mmol) was hydrogenated for 20 h at 40 psi in THF (100 mL) in the presence of 0.2 g of 10% Pd/C. The catalyst was removed by filtration through Celite and filtrate concentrated. The acid was dissolved in 20 mL of anhydrous CH2Cl2. Diisopropylethylamine ((0.88 g, 6.8 mmol) was added followed by pentafluorophenyl trifluoroacetate (1.9 g, 6.8 mmol). After being kept at room temperature for 1 h solvent was evaporated and residue chromatographed on silica (ethyl acetate-hexane) to afford 2.2 g (91%) of 4 as viscous liquid. 1H NMR (DMSO-d6) δ 4.05 (t, J=6 Hz, 2H), 3.04 (t, J=6 Hz, 2H), 2.72 (t, J=6 Hz, 2H), 2.26 (t, J=7 Hz, 2H), 1.78 (q, 2H), 1.38 (s, 9H).

Aufarbeitung

  1. customThe catalyst was removed by filtration through Celite and filtrate
  2. concentrationconcentrated
  3. dissolutionThe acid was dissolved in 20 mL of anhydrous CH2Cl2
  4. additionDiisopropylethylamine ((0.88 g, 6.8 mmol) was added
  5. customsolvent was evaporated
  6. customresidue chromatographed on silica (ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1db908cf5adf43e8b37a7742e4d6e9da
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759126B2

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