Hydrochloric Acid → 5-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid

HRID 420994Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=2)[C:8]2[C:13]([C:14]=1[CH2:15][N:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:17])=[CH:12][C:11]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=2)[C:6]([C:4]([OH:5])=[O:3])=[C:14]3[CH2:15][N:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:17])=[CH:29][CH:28]=1)([CH3:32])([CH3:33])[CH3:31]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-(4-tert-butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (198 mg, 0.36 mmol, see step (d)), NaOH (aq, 1 M, 2 mL) and dioxane (3 mL) was heated at 120° C. for 30 min, cooled, acidified with HCl (aq, 1 M) to pH 5 and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to afford the sub-title compound. Yield 184 mg (98%).

Workup

temperaturecooled
extractionextracted with EtOAc
washThe combined extracts were washed with H2O and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified by chromatography

Sources & evidence

ORD record: ord-95d86dd038224dfd89b3f2d980642fbf
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097623B2

Reaction notes

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