HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Travoprost
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Isopropyl (Z)-7-((1R,2R,3R,5S)-2-((3R,E)-3-(tert-butyldimethylsilyloxy)-4-(3-(trifluoromethyl)-phenoxy)-but-1-enyl)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclopentyl)-hept-5-enoate | HCID 67226385 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | Travoprost | HCID 5282226 | 99% |
Reaction Steps
A mixture of crude compound (11a) (10 g), 2N HCl (37 mL) and isopropanol (IPA) (100 mL) was stirred. The reaction solution was neutralized with saturated aqueous NaHCO3 and extracted twice with EtOAc (80 mL each), once with saturated aqueous NaCl (80 mL) and then the organic layer was concentrated under reduced pressure. The product was purified twice by column chromatography using mixtures of EtOAc and n-heptane to afford Travoprost (HPLC>99.0%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08742143B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-4a676bb44e4c4473b3b3c19a11b1bfec |
| Source note | uspto-grants-2014_06 |