HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine, hydrofluoride (1:1) → 17-Ethyl-1,14-dihydroxy-12-[2'-(4"-(2'"-phenyl-2'"-benzyloxyethyloxy)-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"'-benzyloxyethyloxy)-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 131719452 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 17-Ethyl-1,14-dihydroxy-12-[2'-(4"-(2'"-phenyl-2'"-benzyloxyethyloxy)-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 57133335 | 76% |
Reaction Steps
To a solution of the product from Step A (22 mg) in THF (100 μl) was added hydrogen fluoride/pyridine and the reaction stirred at room temperature for 6 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 (15 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05565560 |
| Source dataset | uspto-grants-1996_10 |
| ORD ID | ord-df4e95de833b4ad7848d81fd400da292 |
| Source note | uspto-grants-1996_10 |