(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)ethanol → (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid

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Preparation of(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid (37A): (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid (4.9 mg) was prepared in a similar manner as compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)acetic acid of Example 29 except using (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)ethanol instead of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol. 1H-NMR 400 MHz (CD3OD) δ 7.95 (m, 1 H), 7.90 (s, 1 H), 7.7-7.6 (m, 6 H), 7.50 (m, 3 H), 7.37 (d, J=8.8 Hz, 1 H), 5.23 (s, 1 H), 2.72 (s, 3 H), 0.99 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C30H27ClNO3: 484.2. Found: 484.2. Preparation of(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol: The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)ethanol (6 mg) and rhodium on alumina (2 mg) in ethanol (1.5 mL) was stirred under 1 atm of hydrogen for 3 hours. Celite was added, and the mixture was filtered and washed with ethyl acetate. Concentration of the mother liquor under reduced pressure gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol (6.5 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H33ClNO2: 474.2. Found: 474.3.

Provenance & Evidence