HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Fluorobenzoyl chloride → 18-(4-Fluorobenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Fluorobenzoyl chloride | HCID 67879 | — |
| Reactant | tert-butyl N-[4-(cyclopropylsulfonylcarbamoyl)-18-hydroxy-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-14-yl]carbamate | HCID 68797769 | — |
| Product | 18-(4-Fluorobenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene | HCID 72445365 | 9.1% |
Reaction Steps
Prepared by way of method I using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.176 mmol) and 4-fluorobenzoyl chloride (42 mg, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 11 mg (9.1%) of 18-(4-fluorobenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 95.0% pure (HPLC), MS m/z 689 (M−H)−, HRMS: calcd. 691.2813 and found 691.2827 (M+H)+, mp 154-156° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772183B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-020d8e0278e94fbcb56e3761b7c5acdd |
| Source note | uspto-grants-2010_08 |