HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoromethanesulfonic anhydride → Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | Methyl {3-(4-chlorophenyl)-5-oxo-4-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate | HCID 59536753 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate | HCID 59536880 | — |
Reaction Steps
At RT, 280 mg (0.74 mmol) of the compound of Example 7A together with 108 mg (0.89 mmol) of 4-N,N-dimethylaminopyridine were initially charged in 5.3 ml of pyridine, 0.31 ml (1.84 mmol) of trifluoromethanesulphonic anhydride were added a little at a time and the mixture was stirred for 12 h. The pyridine was then removed on a rotary evaporator. The residue was taken up in acetonitrile and 1 N hydrochloric acid and purified by preparative HLPC [Method 9]. This gave 230 mg (86% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09180120B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-ffca4b1a1a7548bd8b98035538196ae2 |
| Source note | uspto-grants-2015_11 |