Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 86626882 | HCID 86626882 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 86626885 | HCID 86626885 | 227.1% |
Reaction Steps
Ethyl 4-(2-{(3,5-bis-trifluoromethyl-benzyl)-[2-((S)-1-hydroxymethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (102 mg) is dissolved in methylene chloride (1.5 ml) and thereto is added triethylamine (31 μl), followed by an addition of triphosgene (17 mg) under water-cooling, and the mixture is stirred at room temperature overnight. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (hexane:ethyl acetate=9:1→7:3) to give ethyl 4-(2-{(3,5-bis-trifluoromethyl-benzyl)-[2-((S)-4-ethyl-2-oxo-oxazolidin-3-yl)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (94 mg). MS (m/z): 723 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07906517B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-5614107af99f47308b6a0ea36ba23fbd |
|---|
| Source note | uspto-grants-2011_03 |
|---|