반응 #47235

반응 방정식

6-[(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid methyl ester

6-[(S)-3-Cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid methyl ester

lithium hydroxide monohydrate

hydrochloric acid

→

6-[(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid

수율 39.0%

용매

dichloromethane

tetrahydrofuran

water

반응 조건

후처리

1. 1
   세척washed with saturated sodium chloride solution
2. 2
   기타dried

실험 절차

A solution of 6-[(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid methyl ester (prepared as in Example 10, 62 mg, 0.16 mmol) in tetrahydrofuran (2 mL) was treated with a solution of lithium hydroxide monohydrate (8 mg, 0.18 mmol) in water (1 mL). The mixture was stirred for 1 h. It was then acidified with 2N aqueous hydrochloric acid and diluted with dichloromethane, washed with saturated sodium chloride solution and dried to afford 6-[(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid, (23 mg, 39%) as a white powder: LR-ES-MS m/z calculated for C19H23N3O5 [M]+ 373, observed [M+H]+ 374; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.97 (m, 11H) 3.79 (s, 3H) 4.01 (d, J=17.9 Hz, 1H) 4.33 (d, J=17.7 Hz, 1H) 4.93 (dd, J=10.9, 4.5 Hz, 1H) 5.18 (s, 1H) 8.12 (d, J=8.5 Hz, 1H) 8.24 (dd, J=8.7, 2.3 Hz, 1H) 8.83 (d, J=2.3 Hz, 1H) 11.18 (s, 1H) 12.81 (br. s., 1H).

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