Lithium hydroxide, monohydrate → HCID 22143552, compound

HRID 1825188Notes

Reaction equation

HRID 1825188 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]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22143500HCID 22143500, compound

Product 1

HCID 22143552HCID 22143552, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 86594347Tetrahydrofuran dimethanolSolvent

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).

Workup

  1. customthe organic solvents removed under reduced pressure
  2. customThe white solid which precipitated
  3. filtrationwas collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8a5d926f701e4c348d44e42d89fbca11
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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