Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl propiolate | HCID 13536 | — |
| Reactant | 4-Azido-L-phenylalanine (hydrochloride) | HCID 86585254 | — |
| Product | HCID 86585253 | HCID 86585253 | 53% |
Reaction Steps
4-Azido-L-phenylalanine hydrochloride (0.242 g, 1 mmol) was dissolved in dry DMF (1 mL) and methyl propiolate (0.420 g, 5 mmol) was added. The suspension was stirred 24 h at 45° C. After cooling to room temperature, the solid was filtered, washed with EtOAc and dried (175 mg). The material was suspended in MeOH (15 mL) and thionyl chloride (0.5 mL) was added dropwise. The mixture was refluxed for 3 h, cooled and concentrated under reduced pressure. The residue was triturated with ether to give the title compound as a white solid (175 mg, 53% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06794404B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-476b474defa0409e97d8b106671db285 |
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| Source note | uspto-grants-2004_09 |
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