HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,4-Difluorobenzylamine → (1-Benzyl-3-{[3-(2,4-difluoro-benzylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,4-Difluorobenzylamine | HCID 2733244 | — |
| Reactant | {1-Benzyl-3-[(3-fluoro-4-nitro-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester | HCID 68508884 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1-Benzyl-3-{[3-(2,4-difluoro-benzylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester | HCID 69155346 | 100% |
Reaction Steps
{1-Benzyl-3-[(3-fluoro-4-nitro-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester (7) (0.40 g, 0.67 mmol, 1 equiv) and 2,4-difluoro-benzylamine (0.14 g, 1 mmol, 1.49 equiv) were dissolved in tetrahydrofurane (10 mL). The solution was heated to reflux for 18 h. The solution was concentrated and the crude product was dissolved in dichloromethane (15 mL). The organic layer was washed with saturated NaHCO3 solution (15 mL). The organic layer was separated and evaporated under reduced pressure to yield the title compound (0.48 g, 0.67 mmol, quantitative). LRMS (ES+): m/z 719 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084494B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-47dafd42dc0b4ea084f174b980f37af4 |
| Source note | uspto-grants-2011_12 |