Hydrochloric Acid → 3-Phenyl-3-{5-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-propionic acid

HRID 24049Notes

Reaction equation

C([O:3][C:4](=[O:35])[CH2:5][CH:6]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[CH2:25][CH2:24][CH2:23][NH:22][C:21]=4[N:20]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)C.[OH-].[Na+].Cl>C1COCC1.O>[C:29]1([CH:6]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH2:16][CH2:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[CH2:25][CH2:24][CH2:23][NH:22][C:21]=5[N:20]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:5][C:4]([OH:35])=[O:3])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-phenyl-3-{5-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-propionic acid ethyl ester (0.020 g, 0.04 mmol) and sodium hydroxide (0.01 g, 0.25 mmol) in THF/H2O [1/0.3] (1.3 mL) was stirred at 50° C. for 24 h. The reaction mixture was neutralized with 1.0 N HCl to pH 5 and extracted with ethyl acetate. After removal of solvent, the crude product was purified via column chromatography, eluting with methylene chloride/methanol (95/5) to give the title compound (15% yield) as white solid. 1H NMR (CDCl3) δ 10.76 (br, 1H), 8.16 (br, 1H), 7.57 (br, 1H), 7.10-7.45 (m, 8H), 7.03 (m, 1H), 6.95 (m, 2H), 6.18 (m, 1H), 3.38 (m, 2H), 3.21 (m, 2H), 2.61 (m, 2H), 2.43 (m, 2H), 2.03 (m, 2H), 1.82 (m 2H), 1.70 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C28H30N3O2 440.2 (M+H); found 440.3.

Workup

extractionextracted with ethyl acetate
customAfter removal of solvent
customthe crude product was purified via column chromatography
washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record: ord-e3b8245fe67b449b9b87c416ae1914b4
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855722B2

Reaction notes

Loading…