تفاعل #502130

معادلة التفاعل

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

N,N-bis(2-hydroxyethyl)-p-toluenesulfonamide

1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride

→

title compound

المردود 70.0%

2-((2-Hydroxyethyl)((4-methylphenyl)sulfonyl)amino)ethyl(2S)-2-(6-methoxy(2-naphthyl))propanoate

المردود 70.0%

المذيبات

CH2Cl2

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىpartitioned between CH2Cl2 and HCl (1N)
2. 2
   غسيلThe aqueous layer was washed with CH2Cl2
3. 3
   غسيلthe combined organic extracts were washed with water, brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by column chromatography on silica gel eluting with EtOAC/hexane (1:1)

الإجراء التجريبي

To a solution of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid(naproxen, 5.0 g, 21.7 mmol), N,N-bis(2-hydroxyethyl)-p-toluenesulfonamide (16.89 g, 65.1 mmol) and N,N-dimethylaminopyridine (DMAP, 0.530 g, 4.34 mmol) in CH2Cl2 (250 mL) and DMF (3 mL) at room temperature was added 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDAC, 4.99 g, 26.05 mmol). The reaction mixture was stirred overnight at room temperature, and then partitioned between CH2Cl2 and HCl (1N). The aqueous layer was washed with CH2Cl2 and the combined organic extracts were washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with EtOAC/hexane (1:1) to give the title compound as a thick oil (7.15 g, 15.16 mmol, 70% yield): 1H NMR (300 MHz, CDCl3) δ 7.73 (d, J=8.6 Hz, 2H), 7.66 (m, 1H), 7.67 (d, J=8.6 Hz, 2H), 7.40 (dd, J=1.7, 8.5 Hz, 1H), 7.29 (d, J=8.1 Hz, 2H), 7.18 (dd, J=2.5, 8.8 Hz, 1H), 7.14 (d, J=2.4 Hz, 1H), 4.28 (m, 2H), 3.95 (s, 3H), 3.88 (q, J=7.2 Hz, 1H), 3.38 (m, 2H), 3.09 (t, J=5.1 Hz, 2H), 2.44 (s, 3H), 2.18 (t, J=6.0 Hz, 1H), 1.61 (d, J=7.2 Hz, 3H). Mass spectrum (API-TIS) m/z 472 (MH+), 489 (M+18+).

المصدر