Lithium hydroxide, monohydrate → HCID 22143552, compound
Reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:33]=[CH:32][C:23]4[C:24]([C:28]([O:30]C)=[O:29])=[C:25]([CH3:27])[O:26][C:22]=4[CH:21]=3)[CH:11]=2)=[O:9])[CH2:4]1.O.[OH-].[Li+]>C1COCC1.CO.CO>[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:33]=[CH:32][C:23]4[C:24]([C:28]([OH:30])=[O:29])=[C:25]([CH3:27])[O:26][C:22]=4[CH:21]=3)[CH:11]=2)=[O:9])[CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of methyl 6-[2-(3-methoxypyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-2-methyl-benzofuran-3-carboxylate 89d (540 mg, 1.16 mmole) in THF/MeOH/MeOH (6 ml, 1:1:1) was added lithium hydroxide monohydrate (54 mg, 1.29 mmole). When the ester disappeared by thin layer chromatography (tic), the organic solvents removed under reduced pressure, and the aqueous residue was neutralized with 2N HCl. The white solid which precipitated was collected by filtration and dried under vacuum to give the desired acid (411 mg, 83%). 1H NMR (DMSO-d6) δ 13.02 (1H, bs), 8.57 (1H,d, J=5.3 Hz), 8.05 (1H, s), 7.94 (1H, d, J=8.5 Hz), 7.68 (1H, s), 7.25 (1H, d, J=8.5 Hz), 6.75 (1H, d, J=5.5 Hz), 4.10–3.85 (3H, m), 3.65–3.45 (2H, m), 3.25 (3H, d, J=9.4 Hz), 2.74 (3H, s), 2.15–1.95 (2H,m).