Lithium hydroxide, monohydrate → 3-Methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoic acid

HRID 330179Notes

Reaction equation

HRID 330179 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][CH:27]([C:29](=[O:36])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH3:28])[CH:24]=2)[N:19]([CH3:37])[CH:18]=1)[C:9]([O:11]C)=[O:10]>O.CO.O1CCCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][CH:27]([C:29](=[O:36])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH3:28])[CH:24]=2)[N:19]([CH3:37])[CH:18]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 14882559Methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoate

Product 1

HCID 198706133-Methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoic acidYield 99.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.29 g) in water (5 ml) was added to a solution of methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoate (0.65 g) in methanol (25 ml) and tetrahydrofuran (5 ml). The mixture was stirred under an atmosphere of nitrogen for 48 hr, and the solvents evaporated. The residue was taken up in water (5 ml), acidified with 1M hydrochloric acid (10 ml), and the precipitate which formed isolated by filtration to give the title compound (0.63 g, 94%) as a white powder; mp 85°-95°.

Workup

  1. customthe solvents evaporated
  2. customthe precipitate which formed
  3. customisolated by filtration

Sources & evidence

ORD record
ord-78e0068d84ab423bbedc0145bf8d41aa
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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