Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl acetoacetate | HCID 7757 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 19791786 | HCID 19791786 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59583407 | HCID 59583407 | 68.8% |
Reaction Steps
To a solution of 2-biphenylylmethyl azide (Intermediate 2) (1.1 g, 5.2 mmol) and methyl acetoacetate (0.9 g, 7.8 mmol) in DMSO (10 mL) was added potassium carbonate (2.9 g, 20 mmol). The reaction mixture was stirred at 40° C. for 48 hours. After cooling, water was added and the mixture was extracted with ethyl acetate, the organic layer was dried on sodium sulphate and after filtration was evaporated to dryness. The residue was purified by flash column chromatography eluting with DCM and DCM/MeOH: 98/2 to give the title compound as an oil (1.1 g, 68.7%). LC/MS: m/z 308 (M+H)+, Rt: 3.14 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08486977B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-a1d1b6da6de54929b6d69a9551171335 |
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| Source note | uspto-grants-2013_07 |
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