HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(tert-butyldiphenylsilyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate | HCID 131735010 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate | HCID 69915043 | — |
Reaction Steps
To a solution of compound 42 (0.6 mmol) in dry THF (12 mL) was added dropwise a solution of tetrabutylammonium fluoride (1M in THF, 12 mL). The reaction was stirred at room temperature overnight, and then concentrated. The residue was dissolved in MeOH and purified by semi preparative HPLC (RP18) to yield compound 43, which was used without further purification directly in the next step. MS (ESI, EI+): m/z=379 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09284307B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-eb5f664767214c3197153e4dbb6ab6ee |
| Source note | uspto-grants-2016_03 |