Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 71293456 | HCID 71293456 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | HCID 71293437 | HCID 71293437 | 92.3% |
Reaction Steps
To a solution of Intermediate 18 (0.12 g, 0.19 mmol) in DCM (2.5 mL) and TFA (0.25 mL) was added. The resulting mixture was stirred at RT for 1 hour and then evaporated in vacuo. The resulting residue was taken up in DCM (4 mL), and then triethylamine (105 μL, 0.75 mmol) added, followed by methanesulfonyl chloride (28 μL, 0.36 mmol). The reaction mixture was stirred at RT for 30 mins and then partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM as eluent to yield the title compound as a white solid (106 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09023855B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-ccb75d57cd654b389d8514f3b081efe1 |
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| Source note | uspto-grants-2015_05 |
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