HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon Dioxide → (4s)-2'-(3,3-Dimethylbutyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Racemic 2'-(3,3-dimethylbutyl)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine | HCID 58466165 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (4s)-2'-(3,3-Dimethylbutyl)-7'-(pyrimidin-5-yl)-5h-spiro[oxazole-4,9'-xanthen]-2-amine | HCID 67242781 | 42.9% |
Reaction Steps
Racemic 2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (490 mg) from step 1 was subjected to chromatography using 20:80:0.1 MeOH:CO2:DEA at 70 ml/min on a 20×150 mm ChiralPak AD-H column and 100-bar system pressure. The first peak (RT=1.97 min) provided (4S)-2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (210 mg, 99% ee), and the second peak (RT=4.43 min) provided (4R)-2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (>99% ee).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883782B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-2afbed8d65104159a204f4b83bb64432 |
| Source note | uspto-grants-2014_11 |