Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate | HCID 16211673 | — |
| Reactant | HCID 58994328 | HCID 58994328 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178424503 | HCID 178424503 | 92% |
Reaction Steps
A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 2.20 g, 3.45 mmol) and tetrabutylammonium fluoride hydrate (4.52 g, 17.3 mmol) in 25 mL of THF was stirred at 50° C. for 3 h. After cooling to RT, the mixture was treated with 100 mL of EtOAc and washed with saturated aqueous NH4Cl (20 mL), H2O (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (0-4% MeOH/DCM) to afford the title compound (1.25 g, 92%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C23H28N4O2, 393.2 (M+H). found 393.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08674100B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-001f50f0e960470bbcd22dec8ffbb6a3 |
|---|
| Source note | uspto-grants-2014_03 |
|---|