HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine, hydrofluoride (1:1) → 17-Ethyl-1,14-dihydroxy-12-[2'-(4"-(2"'-phenyl-2"'-oxo-ethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3,1.04,9]octacos-18-ene-2,3,10,16-tetraone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine, hydrofluoride (1:1) | HCID 64774 | — |
| Reactant | 17-Ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2"'-phenyl-2"'-oxo-ethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone | HCID 57120639 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 17-Ethyl-1,14-dihydroxy-12-[2'-(4"-(2"'-phenyl-2"'-oxo-ethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3,1.04,9]octacos-18-ene-2,3,10,16-tetraone | HCID 57273654 | 61.1% |
Reaction Steps
To a solution of the product from Step A (188 mg) in THF (2.8 ml) was added hydrogen fluoride/pyridine and the reaction mixture stirred at room temperature for 24 hours. The reaction was then quenched by the addition of saturated aqueous sodium bicarbonate and extracted into ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated. The crude material was purified by column chromatography on silica gel eluting with 50% hexane:50% ethyl acetate to give the title compound (102 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05693648 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-e5953ae644e44440b248d42ef44b3d65 |
| Source note | uspto-grants-1997_12 |