Reaktion #1018922

Reaktionsgleichung

(S)-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one

periodic acid

chromium trioxide

→

periodic acid chromium trioxide

(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)acetic acid

Ausbeute 87.7%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with 1.5 M K2HPO4 solution
2. 2
   Extraktionextracted with ethyl acetate (2×)
3. 3
   WaschenThe combined organic layer was washed with 1:1 brine/H2O (2×), saturated NaHSO3/brine
4. 4
   Trocknenwas dried (MgSO4)
5. 5
   EinengenConcentration and purification

Vorschrift

A stock solution of periodic acid/chromium trioxide was prepared according to WO 99/52850 by dissolving periodic acid (11.4 g, 50.0 mmol) and chromium trioxide (23 mg, 1.2 mol %) in wet acetonitrile (0.75% H2O) to a volume of 114 mL. This stock solution (0.40 mL) was added to a solution of (S)-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one (8K, 4.4 mg) in wet acetonitrile (1.5 mL, 0.75% H2O) at 0° C. After stirring for 60 min at 0° C., the reaction was quenched with 1.5 M K2HPO4 solution and extracted with ethyl acetate (2×). The combined organic layer was washed with 1:1 brine/H2O (2×), saturated NaHSO3/brine, and was dried (MgSO4). Concentration and purification by prep-HPLC gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)acetic acid (8L) (2 mg). 1H-NMR 300 MHz, (CD3OD) 7.56-7.53 (3H, m), 7.35 (1H, d, J=9.7 Hz), 7.28 (1H, d, J=8.2 Hz), 7.22 (1H, s), 6.43 (1H, d, J=9.8 Hz), 5.06 (1H, s), 2.55 (3H, s), 0.95 (9H, s). LCMS-ESI+ (m/z): [M+H]+ calcd for C22H23ClNO4: 400.9. Found: 400.2; LCMS-ESI− (m/z): [M−H]− calcd for C22H21ClNO4: 398.9. Found: 397.9.

Quelle