HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Chloride → benzyl(4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-[4-(6-methyl-2-pyridinyl)benzyl]-1,3-oxazolidine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 2-Methyl-6-(tributylstannyl)pyridine | HCID 11463183 | — |
| Reactant | benzyl(4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-{4-[(trifluoroacetyl)oxy]benzyl}-1,3-oxazolidine-3-carboxylate | HCID 67407042 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | benzyl(4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-[4-(6-methyl-2-pyridinyl)benzyl]-1,3-oxazolidine-3-carboxylate | HCID 67407091 | 98.1% |
Reaction Steps
A solution containing the product from Example 23I (0.113 g, 0.160 mmol) in DMF (1.5 mL) was treated with LiCl (0.068 g, 1.60 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.034 g, 0.048 mmol), and the product from Example 68A (0.367 g, 0.961 mmol), heated at 110° C. for 16 hours, cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-50% ethyl acetate in dichloromethane to give the title compound (0.102 g, 98% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834043B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-0c98ff6127ff4b42ac3a555bf0a2a13c |
| Source note | uspto-grants-2010_11 |