Lithium hydroxide, monohydrate → 4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid

HRID 1723206Notes

Reaction equation

HRID 1723206 reaction equation
[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>CO.O1CCCC1.O>[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11453373Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Product 1

HCID 112931194-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acidYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoate (0.25 g.) in methanol (5 ml.) and tetrahydrofuran (4 ml.), under an atmosphere of nitrogen, was treated with a solution of lithium hydroxide monohydrate (0.12 g.) in water (2 ml.). The mixture was stirred for 20 hours and then concentrated to remove tetrahydrofuran. The resulting aqueous solution was acidified with 1M hydrochloric acid (20 ml.). The white precipitate which formed was separated by filtration, washed with a little water, and recrystallized from a mixture of toluene and hexane to give the title compound (0.212 g., 88%) as an offwhite powder; m.p. 157°-158° C.

Workup

  1. concentrationconcentrated
  2. customto remove tetrahydrofuran
  3. customThe white precipitate which formed
  4. customwas separated by filtration
  5. washwashed with a little water
  6. customrecrystallized from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-9f36ca9427c84ef1a0a842aae51abb56
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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