Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 66856902 | HCID 66856902 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66857525 | HCID 66857525 | 66% |
Reaction Steps
To a solution of tert-butyl 2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethylcarbamate (53 mg, 0.1 mmol) in tetrahydrofuran was added NaH (300 mg, 12.5 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h. Then iodomethane (1.3 g, 9.15 mmol) was added to the above mixture and the mixture was stirred for 2 h. The reaction was quenched with H2O and extracted with EtOAc to give the organic layer which was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated to give tert-butyl 2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl(methyl)carbamate (36 mg, 66%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575156B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-54b80f55c3934c36a781dbff4b47db43 |
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| Source note | uspto-grants-2013_11 |
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