Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 67365084 | HCID 67365084 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67365317 | HCID 67365317 | — |
Reaction Steps
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(3-chloro-phenyl)-2-methyl-oxazole-4-carboxylic acid (2-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-2H-[1,2,3]triazol-4-yl)-amide (106 mg, 0.20 mmol) in dry THF (1.9 mL) was treated at 0° C. with TBAF (0.39 mL of a 1M solution in THF, 0.39 mmol). The reaction mixture was stirred at 0° C. for 45 min. The mixture was then diluted with EA (10 mL), washed with NaHCO3 (10 mL) followed by brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (19:1 CH2Cl2-MeOH) gave the title compound as a white solide. TLC:rf (19:1 CH2Cl2-MeOH)=0.22. LC-MS-conditions 01: tR=0.93 min; [M+H]+=428.97.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08536209B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-89c6c46c2a094939a7dad70d1bd049ed |
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| Source note | uspto-grants-2013_09 |
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