Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | m-Xylyl bromide | HCID 12099 | — |
| Reactant | m-Xylyl chloride | HCID 12102 | — |
| Reactant | Acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4-aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester hydrochloride | HCID 67353702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71245517 | HCID 71245517 | 57.3% |
Reaction Steps
In a nitrogen atmosphere, intermediate 6 (200 mg, 0.400 mmol) was dissolved in DCM (5 ml), triethylamine (166 μL, 1.20 mmol) and 1-(chloromethyl)-3-methylbenzene (79 μL, 0.60 mmol) were added, and the mixture was heated at 40° C. for 2 hours and at RT for 16 hours. Then triethylamine (138 μL, 1.00 mmol) and 3-methylbenzyl bromide (54 μL, 0.40 mmol) were added to the mixture, and stirring was continued for 2 hours. The reaction mixture was partitioned between water and DCM, and the aqueous layer was extracted with DCM (3×15 mL), and the organic phase was collected and concentrated. The crude was purified by silica gel flash chromatography (eluent DCM/MeOH 99:1) to yield the title compound (130 mg, 57.2% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08710037B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-c8a0c6f5b6494f429e8b6c6ae165a1a8 |
|---|
| Source note | uspto-grants-2014_04 |
|---|
