تفاعل #52266

معادلة التفاعل

methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoate

water

sodium hydroxide

→

title compound

المردود 82.2%

3-[5-(3-{(Benzylamino]carbonylamino}propoxy)indolyl]propanoic acid

المردود 82.2%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter evaporating the tetrahydrofuran
2. 2
   أخرىthe white solid formed
3. 3
   أخرىwas collected
4. 4
   غسيلwashed with water
5. 5
   أخرىdried under high vacuum

الإجراء التجريبي

To the solution of methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoate (80 mg, 0.2 mmol), as prepared in the preceding step, in tetrahydrofuran (5 mL) and water (5 mL) was added sodium hydroxide (20 mg), and the reaction mixture was stirred at ambient temperature for 2 h. After evaporating the tetrahydrofuran, the aqueous solution was acidified (pH 5-6), the white solid formed was collected, washed with water and dried under high vacuum to give the title compound (65 mg, 82%). 1H-NMR (400 MHz, DMSO6) δ 7.21 -7.37 (m, 7H), 7.02 (d, J=2.4 Hz, 1H), 6.78 (dd, J=8.8, 2.4 Hz, 1H), 6.36 (t, J=6.0 Hz, 1H), 6.30 (d, J=2.9 Hz, 1H), 6.06 (t, J=5.7 Hz, 1H), 4.34 (t, J=6.8 Hz, 2H), 4.20 (d, J=6.0 Hz, 2H), 3.96 (t, J=6.2 Hz, 2H), 3.19 (q, J=6.4 Hz, 2H), 2.71 (t, J=6.8 Hz, 2H), 1.83 (t, J=6.5 Hz, 2H). Mass spectrum (LCMS, ESI) Calcd. for C22H25N3O4 396.4 (M+H), found: 396.1.

المصدر