HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloride → t-Butyl 2-[(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydrofuran-3-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 | Thionyl Chloride | HCID 24386 | — |
| Reactant | Butylphosphine | HCID 2784062 | — |
| Reactant | t-Butyl (RS)-2-hydroxy-2-[(3R, 4R)-3-phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate | HCID 53961123 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | t-Butyl 2-[(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate | HCID 18396316 | — |
Reaction Steps
t-Butyl (RS)-2-hydroxy-2-[(3R, 4R)-3-phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate (2.719g) in THF (20ml) was treated with thionyl chloride (1.01g, 0.615ml) and 2,6-lutidine (0.913g, 0.989ml) as described in Example 1(d). Following work-up the crude chloride in dioxan (30ml) was then treated with n-butylphosphine (2.53g, 3.11ml). After purification by flash chromatography with 50, 70% ethyl acetate/hexane then ethyl acetate the title compound was obtained as a pale yellow foam (1.496 g, 40%); vmax (CH2Cl2) 3420, 1762, 1717 (shoulder), 1681 and 1625cm-1. (Mass spectrum: +ve ion (3NOBA, Na+), MH+ (663), MNa+ (685)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06020329 |
| Source dataset | uspto-grants-2000_02 |
| ORD ID | ord-07d9463182334892932a5902cd64c10e |
| Source note | uspto-grants-2000_02 |