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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 888232Generated: October 30, 2026

Hydrochloric Acid → (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acid

https://huagongshe.com/reaction/888232

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantPotassium HydroxideHCID 14797—
Reactantdiisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioateHCID 58487998—
SolventOxolane--water (1/1)HCID 21881883—
Product(2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acidHCID 58487990110.9%

Reaction Steps

To a solution of diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioate (6.98 g; 16.6 mmol; 1.0 eq.) in THF/water (3/1; 140 mL) was added potassium hydroxide (5.59 g; 99.6 mmol; 6.0 eq.). The reaction mixture was then stirred for 14 h at RT. The aq. layers were acidified with an aqueous solution of HCl to pH 2, extracted with EtOAc. The combined organic layers were then dried over MgSO4 and evaporated to give the title compound as an oil (6.19 g), used in the next steps without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08247437B2
Source datasetuspto-grants-2012_08
ORD IDord-b4339f150c964837b0dec952608075ce
Source noteuspto-grants-2012_08