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Sodium Hydroxide → 2-{4-[2-(2-Biphenyl-4-yl-5-Methyloxazol-4-yl)-Ethoxy]-2-Cyclohexylmethyl-phenoxy}-2-Methyl-Propionic Acid

HRID 398146
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 398146
C([O:3][C:4](=[O:43])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[C:27]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:24]([C:20]2[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:43])=[O:3])=[C:10]([CH2:36][CH:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)[CH:11]=3)[N:19]=2)=[CH:29][CH:28]=1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 129668392-{4-[2-(2-Biphenyl-4-yl-5-methyloxazol-4-yl)-ethoxy]-2-cyclohexylmethyl-phenoxy}-2-methyl-propionic acid ethyl ester

Produkt 1

HCID 129668402-{4-[2-(2-Biphenyl-4-yl-5-Methyloxazol-4-yl)-Ethoxy]-2-Cyclohexylmethyl-phenoxy}-2-Methyl-Propionic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of 2-{4-[2-(2-biphenyl-4-yl-5-methyloxazol-4-yl)-ethoxy]-2-cyclohexylmethyl-phenoxy}-2-methyl-propionic acid ethyl ester (0.54 mmol) in ethanol (10 mL) was treated with 2.5 N aqueous NaOH (0.4 mL), and heated at 55° C. for 2 h. The reaction was cooled to ambient temperature and concentrated down to near dryness. The residue was then diluted with ethyl acetate (40 mL) and water (20 mL) and acidified to pH 1 with 1N aqueous HCl. The organic layer was washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give 2-{4-[2-(2-biphenyl-4-yl-5-methyloxazol-4-yl)-ethoxy]-2-cyclohexylmethyl-phenoxy}-2-methyl-propionic acid. 1H NMR (400 MHz, CDCl3) δ8.03-8.05 (m, 2H), 7.67 (d, 2H, J=8.8 Hz) 7.62 (d, 2H, 6.8 Hz), 7.47-7.43 (m, 2H), 7.35-7.39 (m, 1H), 6.77 (d, 1H, J=8.8 Hz), 6.67 (d, 1H, J=2.9 Hz), 6.62 (dd, 1H, J=8.8 Hz, J=2.9 Hz), 4.18 (t, 2H, J=6.4 Hz), 3.00 (t, 2H, J=6.4 Hz), 2.40 (s, 3H), 1.62-1.66 (m, 5H), 1.53 (s, 6H), 1.25 (s, 2H), 1.13-1.18 (m, 4H), 0.85-0.97 (m, 2H), MS (ES) m/e 554.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated down to near dryness
  3. additionThe residue was then diluted with ethyl acetate (40 mL) and water (20 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72ba2ef396894e65901f8351d7902d29
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06610696B2

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