Hydrochloric Acid → 2-(2-(3-Phenyl-7-propylbenzofuran-6-yloxy)ethyl)indole-5-acetic acid

HRID 1275119Notes

Reaction equation

HRID 1275119 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:19][CH2:20][CH2:21][C:22]4[NH:23][C:24]5[C:29]([CH:30]=4)=[CH:28][C:27]([CH2:31][C:32]([O:34]C)=[O:33])=[CH:26][CH:25]=5)=[C:15]([CH2:16][CH2:17][CH3:18])[C:10]=3[O:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CO.[Li+].[OH-].C(OCC)(=O)C>[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:19][CH2:20][CH2:21][C:22]4[NH:23][C:24]5[C:29]([CH:30]=4)=[CH:28][C:27]([CH2:31][C:32]([OH:34])=[O:33])=[CH:26][CH:25]=5)=[C:15]([CH2:16][CH2:17][CH3:18])[C:10]=3[O:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15462901Methyl 2-(2-(3-phenyl-7-propylbenzofuran-6-yloxy)-ethyl)-indole-5-acetate

Product 1

HCID 154629022-(2-(3-Phenyl-7-propylbenzofuran-6-yloxy)ethyl)indole-5-acetic acidYield 0.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 18.6 mg (39.8 mmol) of methyl 2-(2-(3-phenyl-7-propylbenzofuran-6-yloxy)-ethyl)-indole-5-acetate in ca. 2.0 ml of methanol and 1 M aqueous LiOH (79.6 uL) was heated at 60° C. for 16 hours. The mixture was diluted with ethyl acetate and acidified to pH 5-6 with 1 M HCl, washed with water (2 times), brine (1 time) and dried over sodium sulfate and concentrated to afford 11.6 mg of the title compound. (mp=129-130° C.).

Workup

  1. washwashed with water (2 times), brine (1 time)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7df85619b97a4709aef0c255c76daf9b
Source dataset
uspto-grants-2000_12
Patent number
US06160000

Reaction notes

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