Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 71127341 | HCID 71127341 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 71127315 | HCID 71127315 | 73.9% |
Reaction Steps
tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-[5-cyclopropyl-1-(3-isobutylcyclobutyl)-1H-[1,2,3]triazol-4-yl]valerate (233 mg) and tetrahydrofuran (3.0 mL) were mixed. To the mixture were added tetrabutylammonium fluoride (1 M in tetrahydrofuran) (0.444 mL) and 80 v/v % aqueous acetic acid (0.045 mL) at ice temperature. The mixture was stirred at RT overnight. After an addition of brine at ice temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/2) to give the title compound (107 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08604069B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-8904817a67244b9a9f278969b225d92f |
|---|
| Source note | uspto-grants-2013_12 |
|---|