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

HRID 348339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348339
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[S:37][CH:38]=[CH:39][CH:40]=3)=[CH:32][CH:31]=2)=[N:27][C:26]=1[CH2:41][CH2:42]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[CH3:14][C:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:42][CH2:41][C:26]2[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]4[S:37][CH:38]=[CH:39][CH:40]=4)=[CH:32][CH:31]=3)[O:29][C:25]=2[CH3:24])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:23]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 693150933-(4-Hydroxyphenyl)-2-methyl-2-p-tolyloxypropionic acid ethyl esterHCID 86593515Toluene-4-sulfonic acid 2-(5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl)ethyl ester

Produkt 1

HCID 210842662-Methyl-3-(4-{2-[5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl]ethoxy}-phenyl)-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), toluene-4-sulfonic acid 2-(5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 3, Part B) 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 2-methyl-3-(4-{2-[5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl]ethoxy}-phenyl)-2-p-tolyloxy-propionic acid. 1H NMR (400 MHz, CDCl3) δ 8.00 (d, 2H, J=8.4 Hz), 7.71 (d, 2H, J=8.4 Hz), 7.42 (dd, 1H, J=3.8, 1.0 Hz), 7.36 (dd, 1H, J=5.0, 1.0 Hz), 7.26–7.25 (m, 1H), 7.18 (d, 2H, J=8.4 Hz), 7.12 (dd, 1H, J=5.0, 3.8 Hz), 7.05 (d, 2H, J=8.4 Hz), 6.81 and 6.81 (d of Abq, 4H, J=8.8 Hz), 4.23 (t, 2H, J=6.2 Hz), 3.23 and 3.12 (d of Abq, 2H, J=14.0 Hz), 3.07 (t, 2H, J=6.2 Hz), 2.43 (s, 3H), 2.28 (s, 3H), 1.39 (s, 3H). IR (KBr) 3450, 1718, 1681, 1509, 1216 cm−1. HRMS (ES+) m/z exact mass calcd for C33H32NO5S 554.2001, found 554.2015.

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-31ff76ec0d5d47a4ac0c5b7330d8e67e
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176224B2

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