HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(3'-(methylsulfonyl)biphenyl-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-(3'-(methylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate | HCID 59568587 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-tert-Butyl 4-(1-cyano-2-(3'-(methylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate | HCID 59568565 | 74.3% |
Reaction Steps
(S)-tert-Butyl 4-(1-amino-3-(3′-(methylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 23, step (i), 320 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (280 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and the mixture was purified by chromatography on silica eluting with 1:1 ethyl acetate/isohexane as eluent to afford the sub-titled compound (230 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08193239B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-8a13e11c01aa46c595a6a49126ad0636 |
| Source note | uspto-grants-2012_06 |