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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 517375Generated: October 25, 2026

p-Toluenesulfonic acid monohydrate → Travoprost

https://huagongshe.com/reaction/517375

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acid monohydrateHCID 521998—
Reactant(Z)-isopropyl 7-((1R,2R,3R,5S)-3,5-bis((triethylsilyl)oxy)-2-((R,E)-3-((triethylsilyl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoateHCID 131733340—
SolventAcetoneHCID 180—
SolventWaterHCID 962—
ProductTravoprostHCID 528222692.7%

Reaction Steps

The product of Example 11 (0.8 g) was dissolved in 10 ml acetone and 2 ml water, followed by addition of 0.1 g p-toluenesulfonic acid monohydrate. The reaction solution was stirred at room temperature for 1 hour and concentrated until two separate layers were observed. 30 ml ethyl acetate was added for extraction and phase separation. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and subjected to vacuum evaporation for removal of the solvent until dryness. The crude Travoprost was purified by column chromatography and then concentrated under reduced pressure to provide 0.44 g of Travoprost. UPLC (ACQUITY UPLC HSS C18) analysis of the product showed that no isomer and impurities were detectable and the purity was higher then 99.9%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09115109B2
Source datasetuspto-grants-2015_08
ORD IDord-4679549259c54a2a943f38a28c952546
Source noteuspto-grants-2015_08