HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → [3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester | HCID 67985290 | — |
| Reactant | 1,5-Bis-benzyloxy-2-isopropyl-4-azido-benzene | HCID 71534202 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | [3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester | HCID 117678191 | 62% |
Reaction Steps
A solution of 1,5-bis-benzyloxy-2-isopropyl-4-azido-benzene (373 mg, 1 mmol) and ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester (275 mg, 0.91 mmol) in DMF (2.5 ml) was flushed with nitrogen three times as previously described before adding [Cp*Ru]4 (49 mg, 0.045 mmol) and repeating the three cycle-degassing with nitrogen. The reaction mixture was stirred at RT until completion (i.e., monitored by TLC). AcOEt and H2O were then added. The organic phase was extracted four times with AcOEt, washed with water (three times) and brine (once) and dried over Na2SO4. The solvent was removed under reduced pressure and the reaction mixture was purified by column chromatography (PE/AcOEt:60/40). The title compound was obtained as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09302998B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-9b1d09c803e44762a33b85a15dc5b346 |
| Source note | uspto-grants-2016_04 |