HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Bis(diphenylphosphino)butane → ({2-[({(3s,7r,8r,9s)-8-(Allyloxy)-7-benzyl-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Bis(diphenylphosphino)butane | HCID 82124 | — |
| Reactant | ({2-[({(3S,7R,8R,9S)-7-benzyl-8-(hydroxy)-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate | HCID 69801412 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | ({2-[({(3s,7r,8r,9s)-8-(Allyloxy)-7-benzyl-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate | HCID 59989566 | 68% |
Reaction Steps
Compound 8 was prepared in 68% yield using Compound 3 (150 mg, 0.29 mmol) with dppb (12 mg, 0.03 mmol), Pd2dba3 (5.30 mg, 0.006 mmol) and ethyl methallylcarbonate (41 mg, 0.31 mmol). Purification by flash column chromatography on silica gel eluting with a mixture of hexane-acetone (1:1) gave a white foam: MS: (M+1)+=557, (M−1)+=555. Spectral data were consistent with the assigned structure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06903219B2 |
| Source dataset | uspto-grants-2005_06 |
| ORD ID | ord-3f1afc5605e34e63adaf46e0a03ecde4 |
| Source note | uspto-grants-2005_06 |