HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl azide → (S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl azide | HCID 12152 | — |
| Reactant | (2S)-2-{[(tert-butoxy)carbonyl]amino}pent-4-ynoic acid | HCID 2734488 | — |
| Reactant | Sodium Ascorbate | HCID 23667548 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 2-Methylpropan-2-ol--water (1/1) | HCID 71401949 | — |
| Product | (S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid | HCID 68599866 | — |
Reaction Steps
A mixture of 430 mg Boc-L-propargylglycine, 269 mg benzyl azide, 36 mg copper(II)acetate and 80 mg sodium ascorbate in 15 ml water/t-BuOH (1:1) was stirred for 12 h at RT. The reaction mixture was diluted with ethyl acetate, washed with brine (2×) and the aqueous phase reextracted with ethyl acetate. The crude product obtained after evaporation of the solvent was pure enough for the subsequent transformation. Yield: 855 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08669266B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-dff70ad1aa5a4e628f13b9d28dfbcbba |
| Source note | uspto-grants-2014_03 |