تفاعل #502126

معادلة التفاعل

N-hydroxyphthalimide

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

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

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title compound

المردود 47.0%

1,3-Dioxobenzo(c)azolidin-2-yl(2S)-2-(6-methoxy(2-naphthyl))propanoate

المردود 47.0%

المذيبات

CH2Cl2

DMF

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was then dissolved in EtOAc
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   أخرىThe residue after evaporation of the solvent
7. 7
   أخرىwas chromatographed on silica gel eluting with EtOAc:hexane (1:1)

الإجراء التجريبي

A mixture of N-hydroxyphthalimide (7.1 g, 43.4 mmol), (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (naproxen, 10 g, 43.4 mmol) and N,N-dimethylaminopyridine (DMAP, 5.3 g, 43.4 mmol) in CH2Cl2 (70 mL) and DMF (30 mL) at 0° C. was treated with 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (8.3 g, 43.4 mmol) in CH2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 16 hours and the solvent was evaporated under vacuum. The residue was then dissolved in EtOAc, washed with brine, dried over Na2SO4 and filtered. The residue after evaporation of the solvent was chromatographed on silica gel eluting with EtOAc:hexane (1:1) to give the title compound (7.6 g, 47% yield) as a white solid. Mp 110-112° C. 1H NMR (300 MHz, d6-DMSO) δ 7.80-8.06 (m, 7H), 7.50 (dd, J=1.7 and 8.5 Hz, 1H), 7.32-7.37 (m, 1H), 7.20 (dd, J=2.5 and 9.0 Hz, 1H), 4.50 (q, j=7.1 Hz, 1H), 3.89 (s, 3H), 1.64 (d, J=7.1 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) δ 171.2, 161.8, 157.5, 153.0, 135.5, 133.6, 133.5, 129.3, 128.4, 128.2, 127.3, 126.1, 126.0, 124.0, 119.0, 105.8, 55.2, 41.8, 18.6. Mass spectrum (API-TIS) m/z 376 (MH+), 393 (MNH4+).

المصدر