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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1590102Generated: October 30, 2026

Hydrochloric Acid → 3-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

https://huagongshe.com/reaction/1590102

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantLithium HydroxideHCID 3939—
ReactantTetrahydrofuranHCID 8028—
Reactant3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl esterHCID 11762500—
SolventMethanolHCID 887—
Product3-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acidHCID 14980576—

Reaction Conditions

Temperature80 °C

Reaction Steps

The ester from Step 1 (51.3 g) was hydrolysed using 325 mL THF, 600 mL MeOH and 325 mL of 1N LiOH solution. The mixture was heated to 80° C. for 3 hours, then cooled, acidified with 1N HCl and extracted with 3×200 mL EtOAc. The organic phase was washed with H2O (2×150 mL) and dried (MgSO4). After removal of the solvent the title compound was obtained as a white solid, m.p. 190°-191° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05202321
Source datasetuspto-grants-1993_04
ORD IDord-8592fba9e3d54c5fb7657ddaf1731e85
Source noteuspto-grants-1993_04