HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate | HCID 90354174 | — |
| Solvent | Carbon Dioxide | HCID 280 | — |
| Product | tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate | HCID 90354174 | — |
| Product | tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate | HCID 90354440 | — |
Reaction Steps
tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate (890 mg, 2.00 mmol) was separated into its respective enantiomers by SFC column chromatography (20% ethanol in CO2 on chiral IC-H 2.1×25 cm column, 5 uM particle size) to afford tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate (Enantiomer 1, elution time 8.31 minutes) and tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate (Enantiomer 2, elution time 9.93 minutes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216173B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-cbc639ede30a4e7c9a8cbf6b8282c6e4 |
| Source note | uspto-grants-2015_12 |