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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 486094Generated: October 30, 2026

Hydrochloric Acid → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid

https://huagongshe.com/reaction/486094

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantMethanolHCID 887—
ReactantMethyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoateHCID 19097505—
SolventLithium HydroxideHCID 3939—
SolventTetrahydrofuranHCID 8028—
Product3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acidHCID 19097504—

Reaction Steps

A solution of the ester from Step 1 (22.5 g) in 118 mL 1N LiOH, 120 mL THF, and 65 mL MeOH was heated at 60° C. for 2 hours. The mixture was cooled, poured onto 1N HCl, and extracted with EtOAc (3×). After washing the organic phase twice with brine, the solution was dried (MgSo4) and evaporated. The residue was swished with ether/hexane 1:2 to give the title compound as a solid; m.p. 196.5°-198° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05290798
Source datasetuspto-grants-1994_03
ORD IDord-9c6cf8e6006f4b808bb9d24f0059472c
Source noteuspto-grants-1994_03