Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | HCID 69061026 | HCID 69061026 | — |
| Product | HCID 131727649 | HCID 131727649 | — |
Reaction Steps
A solution of ethyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (1.2 g, 3.04 mmol; Example 12, step 12), diisopropylethylamine (0.37 g, 3.65 mmol), and diphenylphosphoryl azide (1.00 g, 3.65 mmol) in a 1:1 mixture of dioxane and tert-butanol (30 mL) was heated in an oil bath 90° C. for 3 hours. The reaction mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in dichloromethane. Collection and concentration of appropriate fractions provided the titled compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07598264B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-70b8656cd8bf409eb888898bc7847a56 |
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| Source note | uspto-grants-2009_10 |
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