HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Methylisoxazole-3-carbonyl chloride → 18-(5-Methylisoxazole-3-carbonyloxy)-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 | 5-Methylisoxazole-3-carbonyl chloride | HCID 2736894 | — |
| 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-(5-Methylisoxazole-3-carbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene | HCID 72445406 | 26.1% |
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, 0.175 mmol) and 5-methylisoxazole-3-carbonyl chloride (188 mg, 1.06 mmol). The final trituration (diethyl ether/hexane) and filtration gave 31 mg (26%) of 18-(5-methylisoxazole-3-carbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 99.9% pure (HPLC), MS m/z 676 (M−H)−, HRMS: calcd. 678.2809 and found 678.2795 (M+H)+, mp 157-159° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772183B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-a62d9e5cc7a648419e172ab0ec646570 |
| Source note | uspto-grants-2010_08 |