Lithium hydroxide, monohydrate → 3-[3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acid

HRID 1714073Notes

Reaction equation

HRID 1714073 reaction equation
O.[OH-].[Li+].[CH:4]1([C:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:16][CH:17]=3)[N:12]([CH2:23][CH2:24][C:25]([O:27]C)=[O:26])[C:11]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][NH:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>C1COCC1.O>[CH:4]1([C:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:16][CH:17]=3)[N:12]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C:11]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][NH:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68508941methyl 3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

Product 1

HCID 685099363-[3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (1 eq) was added to a solution of methyl 3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate in a mixture THF:H2O (4:1, 0.1 M). The mixture stirred at RT for 1 h. The reaction was quenched with 1 N HCl and the solvent evaporated in vacuo. The residue was washed with the minimum amount of Et2O and the solid residue filtered to obtain the title compound (82%); MS (ES+) m/z 506 (M+H)+.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. customthe solvent evaporated in vacuo
  3. washThe residue was washed with the minimum amount of Et2O
  4. filtrationthe solid residue filtered

Sources & evidence

ORD record
ord-110c2a7c3b8e4fe3bc45a482901fa260
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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