HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4'-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl N-(triethylammoniosulfonyl)carbamate | HCID 2724994 | — |
| Reactant | (S)-tert-Butyl 4-(1-amino-3-(4'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate | HCID 59568597 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-tert-Butyl 4-(1-cyano-2-(4'-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate | HCID 59568556 | 62.3% |
Reaction Steps
(S)-tert-Butyl 4-(1-amino-3-(4′-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 3, step (iv), 0.70 g) in dichloromethane (15 mL) was treated with Burgess' reagent (0.356 g) and the mixture was stirred at room temperature for 6 h. Additional Burgess' reagent (0.15 g) was added and the reaction was stirred overnight. The mixture was absorbed onto silica and purified by chromatography on silica eluting with 33% ethyl acetate in isohexane and then 100% ethyl acetate to afford the sub-titled compound as a solid (0.420 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08193239B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-1cc20313a10549d48e76ba2b7f716b52 |
| Source note | uspto-grants-2012_06 |