Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycine | HCID 750 | — |
| Reactant | Glycine tert-butyl ester hydrochloride | HCID 2725036 | — |
| Reactant | HCID 67099912 | HCID 67099912 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67099576 | HCID 67099576 | — |
Reaction Steps
Ethyl 6-chloro-1-cyano-4-hydroxy-1-methyl-2-oxo-naphthalene-3-carboxylate (0.165 g, 0.54 mmol) was dissolved in 1,4-dioxane (30 mL), and glycine tert-butyl ester hydrochloride (0.090 g, 0.54 mmol) and TEA (TEA) (0.11 mL, 0.81 mmol) were added. The reaction was stirred overnight at 70° C. The reaction was stirred for 18 hours. Another 0.5 equivalents of glycine and one equivalent of TEA were added, and the reaction was stirred at 105° C. for 1 hour. The solvent was then removed, and the crude residue was dissolved in EtOAc and washed with water (3×25 mL), dried with MgSO4, and concentrated. The crude product was purified by silica flash chromatography using the 10-50% EtOAc/hexanes. MS m/e=392 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07928139B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-1eb65088677142539408c94af165568c |
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| Source note | uspto-grants-2011_04 |
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