Hydrochloric Acid → 2-Carboxymethyl-1-(4-diethylaminophenyl)-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid

HRID 420906Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:13]=2)[N:8]([C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:28][CH:27]=2)[C:7]=1[CH2:37][C:38]([O:40]CC)=[O:39])=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[C:38]([CH2:37][C:7]1[N:8]([C:26]2[CH:27]=[CH:28][C:29]([N:32]([CH2:33][CH3:34])[CH2:35][CH3:36])=[CH:30][CH:31]=2)[C:9]2[C:14]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][C:12]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=1)=[CH:11][CH:10]=2)([OH:40])=[O:39]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid ethyl ester (150 mg, 0.26 mmol, see step (c) above), NaOH (aq, 2 M, 2 mL) and dioxane (2 μL) was stirred at 120° C. for 6 h, cooled and acidified with HCl (aq, 1 M) to pH 4 and extracted with EtOAc. The combined extracts were washed with water and brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound as a gray powder. Yield 90 mg (66%), mp 234-236° C.

Workup

temperaturecooled
extractionextracted with EtOAc
washThe combined extracts were washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified by chromatography

Sources & evidence

ORD record: ord-597a341369ef4ca0860a0abe90ebcd52
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097623B2

Reaction notes

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