Isopropanol → (S)-ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoate

HRID 731204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731204
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[O:19][CH:18]=[N:17][CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.CC(O)C>CCCCCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]2[O:19][CH:18]=[N:17][CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 3776IsopropanolHCID 57835798Ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoate

Produkt 1

HCID 57835908(S)-ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoateAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Racemic compound 75.4 (1.3 g, 5 mmol) was separated on a semi-preparatory chiral CHIRALCEL OJ-H column (30×250 mm), using 20% i-PrOH in hexane as eluant. Eluant containing the peak with greater retention time was concentrated and compound 75.5 (620 mg, 2.38 mmol) was obtained as off-white solid. The absolute configuration was assigned by analogy to other GPR40 agonist compounds. MS ESI (pos.) m/e 262.1 (M+H).

Aufarbeitung

  1. additionEluant containing the peak with greater retention time
  2. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-427b8859cbb144aebdb26a143f1bbbcb
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582803B2

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