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Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl ester → HCID 12966849, Verbindung

HRID 2229048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2229048
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[CH3:21][C:22]1[O:26][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)=[N:24][C:23]=1[CH2:39][CH2:40]OS(C1C=CC(C)=CC=1)(=O)=O>CCO>[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:31]=[CH:32][C:27]([C:25]2[O:26][C:22]([CH3:21])=[C:23]([CH2:39][CH2:40][O:1][C:2]3[CH:3]=[CH:4][C:5]([O:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:7]=3)[N:24]=2)=[CH:28][CH:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 12966835Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl esterHCID 22633482HCID 22633482, Verbindung

Produkt 1

HCID 12966849HCID 12966849, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
67.5 °C

Versuchsvorschrift

A mixture of 2-(5-hydroxy-biphenyl-2-yloxy)-2-methyl-propionic acid (80 mg, 0.26 mmol), toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-yl)ethyl ester (0.22 mmol) (see Ex. 1, part F), and 1,5,7-triazobicyclo[4.4.0]dec-5-ene bound to polystyrene (200 mg, 2.6 mmol/g resin, Fluka) was diluted with absolute EtOH (2 mL) and was heated at 65-70° C. for 20 h. The warm mixture was filtered through a cotton plug, and the resin was washed with EtOH (2 mL). The combined filtrates were treated with aqueous 5N NaOH (0.3 mL), heated at 55° C. for 1.5 h, cooled to ambient temperature, and concentrated in vacuo. The residue was treated with ice water (1 mL) and acidified with 5N aqueous HCl (0.5 mL). The mixture with CH2Cl2 (1 mL) was transferred to a ChemElute cartridge (3 g) and eluted with CH2Cl2. The eluent was concentrated to crude product which was purified by mass guided HPLC to afford a white foam. 1H NMR (400 MHz, CDCl3) δ1.26 (s, 6H), 2.44 (s, 3H), 3.10 (t, 2H, J=5.9 Hz), 4.28 (t, 2H, J=6.1 Hz), 6.81 (dd, 1H, J=2.9, 8.8 Hz), 6.86 (d, 1H, J=2.9 Hz), 7.01 (d, 1H, J=8.8 Hz), 7.30-7.48 (m, 8H), 7.63 (d, 2H, J=7.3 Hz), 7.70 (d, 2H, J=8.3 Hz), 8.11 (d, 2H, J=8.3 Hz); MS (ES) m/e [M−1].

Aufarbeitung

  1. filtrationThe warm mixture was filtered through a cotton plug
  2. washthe resin was washed with EtOH (2 mL)
  3. additionThe combined filtrates were treated with aqueous 5N NaOH (0.3 mL)
  4. temperatureheated at 55° C. for 1.5 h
  5. temperaturecooled to ambient temperature
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with ice water (1 mL)
  8. washeluted with CH2Cl2
  9. concentrationThe eluent was concentrated to crude product which
  10. customwas purified by mass
  11. customto afford a white foam

Quellen und Nachweise

ORD-Eintrag
ord-e876f980ac1941c4bf03d3a9d9eb4de6
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06417212B1

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