HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Propanol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)- (9CI) → (S)-1-(2-((1-((tert-butyldimethylsilyl)oxy)propan-2-yl)oxy)-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Propanol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)- (9CI) | HCID 13175136 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 1-(2-fluoro-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one | HCID 58287174 | — |
| Reactant | 2-(2-chloro-4-((4-(((7R,8aS)-5,5-dimethyloctahydroindolizin-7-yl)amino)-5-fluoropyrimidin-2-yl)amino)phenoxy)ethan-1-ol | HCID 71811286 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (S)-1-(2-((1-((tert-butyldimethylsilyl)oxy)propan-2-yl)oxy)-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one | HCID 86704539 | — |
Reaction Steps
A similar procedure as detailed above for Compound 133 was used. 1-(2-fluoro-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one (prepared according to US patent application 20110130415) (239 mg, 1.0 mmol), potassium tert-butoxide (146 mg, 1.2 mmol) and (S)-1-((tert-butyldimethylsilyl)oxy)propan-2-ol (Milestone PharmaTech) (209 mg, 1.1 mmol) in THF (10 mL) was stirred for 2 hr at room temperature to give the product after workup (yield assumed quantitative=410 mg). The product was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321763B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-1220608ed181424c990594f33263b084 |
| Source note | uspto-grants-2016_04 |