Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tryptamine | HCID 1150 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Acetylglycine | HCID 10972 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11242389 | HCID 11242389 | 78% |
Reaction Steps
Diphenylphosphorylazide (5.8 ml, 27.5 ml) and triethylamine (3.85 ml, 27.5 ml) were added in succession to a mixture of tryptamine (4.32 g, 27 mmol) and N-acetylglycine (3.3 g, 28 mmol) in DMF (100 ml) cooled to 0° C. The mixture was stirred under nitrogen at ambient temperature for 12 h, then the solvent was eliminated under reduced pressure. The residue obtained was flash chromatographed on silica gel to produce the expected product (m=5.5 g, 21 mmol), giving a yield of 78%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07291627B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-ae2574ab53e94c1987a5b532049724f5 |
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| Source note | uspto-grants-2007_11 |
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