HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloride → 4-Methoxybenzyl 2-[(3R,4R)-3-Phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | 2,6-Lutidine | HCID 7937 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 4-Methoxybenzyl (2RS)-2-Hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahYdrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate | HCID 86754953 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-Methoxybenzyl 2-[(3R,4R)-3-Phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate | HCID 86755105 | 47% |
Reaction Steps
4-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(2RS,3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate (10.406g) was converted to it's chloride with thionyl chloride (3.34g, 2.02ml) and 2,6-lutidine (3.00g, 3.25ml) in tetrahydrofuran (100ml) as described in Example 6(c). The crude chloride in dioxan (80ml) was then converted to the product with tri-n-butylphosphine (6.98ml) also described in 6(c). Flash chromatography on silica gel afforded the title compound as a foam (6.525g, 47%). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (763)].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06020329 |
| Source dataset | uspto-grants-2000_02 |
| ORD ID | ord-472f4b2582904bcaa8d23cc81ad68c40 |
| Source note | uspto-grants-2000_02 |