Sodium Hydroxide → 3-Chloro-4-((1-ethyl-3-indolylcarbonyl)amino)phenylacetic acid

HRID 1372690Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:24][C:25]([O:27]C)=[O:26])[CH:7]=[CH:8][C:9]=1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][CH3:23])[CH:14]=1)=[O:12]>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:24][C:25]([OH:27])=[O:26])[CH:7]=[CH:8][C:9]=1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][CH3:23])[CH:14]=1)=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

In THF (6.0 ml) was dissolved methyl 3-chloro-4-((1-ethyl-3-indolylcarbonyl)amino)phenylacetate. To the resulting solution was added 0.25N NaOH (6.0 ml) at room temperature. After stirring at 50° C. for 18 hours, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl (2.0 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and then, dried under reduced pressure to give 3-chloro-4-((1-ethyl-3-indolylcarbonyl)amino)phenylacetic acid (250.7 mg, 94%) as a brown amorphous substance.

Workup

temperaturethe reaction mixture was cooled to room temperature
distillationdistilled under reduced pressure
customto remove the solvent
customThe crystals thus precipitated
filtrationwere collected by filtration under reduced pressure
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-9f793498661c4337876eef8b52d05178
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

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