Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate synthesis
- Product Name:Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate
- CAS Number:106685-41-0
- Molecular formula:C29H30O3
- Molecular Weight:426.55
106685-40-9
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18107-18-1
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106685-41-0
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Yield:106685-41-0 79%
Reaction Conditions:
in tetrahydrofuran;methanol at 0 - 20; for 1 h;
Steps:
1.5 Methyl 6-(3-(adamantan-l-yl)-4-methoxyphenyl)-2-naphthoate (5).
To a solution of adapalene (50 mg, 0.121 mmol) in 4: 1 THF/MeOH (0.4 mL) at 0 °C was added TMSCH2N2 (0.15 mL, 0.290 mmol) and the reaction was warmed to room temperature over 1 hour. The reaction mixture was concentrated, IN HCl was added, and was extracted with EtOAc 3x. The combined organic layers were washed with water and brine, dried over Na2S04, filtered, and concentrated; yielding the title compound as a white solid (41 mg, 79% yield). NMR (500 MHz, CDC13) δ 8.61 (s, 1H), 8.07 (dd, J = 8.6, 1.7 Hz, 1H), 8.03 - 7.96 (m, 2H), 7.92 (d, J = 8.6 Hz, 1H), 7.80 (dd, J = 8.5, 1.8 Hz, 1H), 7.60 (d, J = 2.4 Hz, 1H), 7.55 (dd, J = 8.4, 2.4 Hz, 1H), 7.00 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H), 2.19 (s, 6H), 2.10 (s, 3H), 1.80 (s, 6H); 13C NMR (125 MHz, CDC13) δ 167.44, 159.03, 141.51, 139.11, 136.06, 132.67, 131.35, 130.95, 129.82, 128.33, 127.02, 126.59, 126.09, 125.84, 125.68, 124.84, 112.21, 55.27, 52.31, 40.72, 37.25, 29.23; HRMS Accurate mass (ES+): Found 427.2268, C29H3i03 (M+H+) requires 427.2273.
References:
AUSUBEL, Frederick M.;KIM, Wooseong;MYLONAKIS, Eleftherios;WUEST, William M. WO2018/213609, 2018, A1 Location in patent:Page/Page column 93
33626-98-1
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106685-41-0
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932033-57-3
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106685-41-0
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106685-41-0
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106685-41-0
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