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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 274417Generated: October 31, 2026

Hydrochloric Acid → 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoic acid

https://huagongshe.com/reaction/274417

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantMethanolHCID 887—
ReactantLithium HydroxideHCID 3939—
Reactant3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(pyridin-2-ylmethyoxy)indol-2-yl]-2,2-dimethylpropanoic acid allyl esterHCID 15229441—
SolventTetrahydrofuranHCID 8028—
Product3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoic acidHCID 9828630—

Reaction Steps

The compound from Step 1 (133 mg) was dissolved in THF (5 mL), MeOH (3 mL), and 1N LiOH (1.2 mL) and heated at 55° C. for 1 hour. After cooling to room temperature, the mixture was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated to dryness. The residue was swished in ether/hexane, affording the title compound as a white solid, m.p. 186.2°-187.7° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05389650
Source datasetuspto-grants-1995_02
ORD IDord-3b3f223e6a3d453a8769b4920cc904fe
Source noteuspto-grants-1995_02