Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 420994Generated: October 31, 2026

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

https://huagongshe.com/reaction/420994

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium HydroxideHCID 14798—
Reactant5-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterHCID 66657716—
Solvent1,4-DioxaneHCID 31275—
Product5-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acidHCID 66657582—

Reaction Conditions

Temperature120 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08097623B2
Source datasetuspto-grants-2012_01
ORD IDord-95d86dd038224dfd89b3f2d980642fbf
Source noteuspto-grants-2012_01