Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate | HCID 10335849 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86762376 | HCID 86762376 | 76% |
Reaction Steps
(S)-2-Phenyl-2-tert-butoxycarbonylaminoethyl methanesulfonate (15.77 g, 0.05 mol) was dissolved in 50 mL DMF followed by the addition of sodium azide (19.5 g, 0.3 mol). The mixture was stirred for 24 hrs at 55° C., cooled to room temperature, poured into cold water (500 mL) and stirred vigorously for 20 minutes. Precipitate was collected by filtration, washed with water and dried, affording 9.97 g of the title compound as a white solid. Yield: 76%; (MH)+=263; 1H NMR (DMSO-d6): 1.37 (s, 9H), 3.36-3.50 (m, 2H), 4.69-4.75 (m, 1H), 7.23-7.36 (m, 5H), 7.65-7.68 (d, J=9.2 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09095575B2 |
|---|
| Source dataset | uspto-grants-2015_08 |
|---|
| ORD ID | ord-8364dc09c1dc4d2d89d557ecc4b19c5d |
|---|
| Source note | uspto-grants-2015_08 |
|---|