Potassium Carbonate → 3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-p-tolyloxy-propionic acid

HRID 348340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348340
C([O:3][C:4](=[O:23])[C:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)C.[CH3:24][C:25]1[O:29][C:28]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)=[N:27][C:26]=1[CH2:42][CH2:43]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[C:33]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:34]=[CH:35][C:30]([C:28]2[O:29][C:25]([CH3:24])=[C:26]([CH2:42][CH2:43][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C:5]([CH3:14])([O:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=4)[C:4]([OH:3])=[O:23])=[CH:12][CH:11]=3)[N:27]=2)=[CH:31][CH:32]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12966835Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl esterHCID 693150933-(4-Hydroxyphenyl)-2-methyl-2-p-tolyloxypropionic acid ethyl ester

Produkt 1

HCID 210842683-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-p-tolyloxy-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture 2-(p-tolyloxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester (0.030 mmol) (see Ex. 35, Part C), toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 1, Part I) and 325 mesh K2CO3 (0.084 g, 0.60 mmol) in ethanol (2 mL) was heated to reflux for 24 h under N2. Aqueous 5N NaOH (0.5 mL) and additional ethanol (1 mL) was added to the reaction mixture and it was heated at reflux for an additional 2 h. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with aqueous 1 N HCl (5 mL), extracted with water and CH2Cl2 and the organic layer dried by passing it through a Varian Chem Elut 1003 cartridge. The solvent was removed in vacuo to give 3-{4-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-p-tolyloxy-propionic acid. 1H NMR (400 MHz, CDCl3) δ 8.87 (bs, 1H), 8.07 (d, 2H, J=8.6 Hz), 7.72 (d, 2H, J=8.6 Hz), 7.65–7.63 (m, 2H), 7.50–7.38 (m, 3H), 7.19 (d, 2H, J=8.4 Hz), 7.04 (d, 2H, J=8.0 Hz), 6.82 (d, 2H, J=8.4 Hz), 6.80 (d, 2H, J=8.0 Hz), 4.23 (t, 2H, J=6.0 Hz), 3.24 and 3.22 (d of Abq, 2H, J=14.0 Hz), 3.09 (t, 2H, J=6.0 Hz), 2.45 (s, 3H), 2.28 (s, 3H), 1.38 (s, 3H). IR (KBr) 3450, 2924, 1719, 1682, 1509, 1207 cm−1. HRMS (ES+) m/z exact mass calcd for C35H34NO5 548.2437, found 548.2455.

Aufarbeitung

  1. temperatureto reflux for 24 h under N2
  2. temperaturewas heated
  3. temperatureat reflux for an additional 2 h
  4. temperatureThe reaction was cooled
  5. customthe solvent removed in vacuo
  6. extractionextracted with water and CH2Cl2
  7. customthe organic layer dried
  8. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a490bd5b0d244e7fbdc5a9b5f2910a93
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176224B2

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