Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | p-Toluenesulfonyl azide | HCID 13661 | — |
| Reactant | Butanoic acid, 3-oxo-4-(phenylmethoxy)-, 1,1-dimethylethyl ester | HCID 12035485 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 56622760 | HCID 56622760 | 69% |
Reaction Steps
5.54 ml (40 mmol - 2 equivalents) of triethylamine were added dropwise to a solution, which had been cooled to 0° C., of 5.29 g (20 mmol) of tert.-butyl 4-benzyloxyacetoacetate and 4.34 g (22 mmol) of p-toluenesulphonyl azide in 40 ml of anhydrous acetonitrile. The mixture was stirred at 0° C. for 30 min, 8 g of kieselguhr were added, and evaporation in vacuo and chromatography on 100 g of silica gel (toluene:ethyl acetate 95:5) were carried out. 3.98 g (69%) of the title compound were obtained as colorless crystals, melting point: 68° C., Rf: 0.31 (toluene:ethyl acetate 95:5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04841042 |
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| Source dataset | uspto-grants-1989_06 |
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| ORD ID | ord-6c051703d2774d8492ed4de398a5acc3 |
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| Source note | uspto-grants-1989_06 |
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