Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 3-(4-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)propanoic acid | HCID 22282734 | — |
| Reactant | HCID 86594240 | HCID 86594240 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86591771 | HCID 86591771 | 100% |
Reaction Steps
2.70 g (9.5 mmol) of 3-(4-tert-butyloxycarbonylaminomethylphenyl)propionic acid (starting compound A6) are dissolved in 40 ml of DMF, and 2.7 ml of triethylamine are added. After stirring for 5 min., 3.63 g of HBTU are added and, after a further 5 min., 2 g of (2S,4S)-4-azidoproline methyl ester hydrochloride. Stirring at RT overnight is followed by addition of ethyl acetate and water and separation of the phases. The organic phase is washed once each with 1N sodium hydroxide solution, 1N hydrochloric acid solution, saturated sodium bicarbonate solution and saturated brine. Drying over magnesium sulfate is followed by concentration and drying under high vacuum. 4.1 g of the title compound are obtained as a pale orange oil. The mass spectrum shows the molecular peak MNH4+ at 449 Da.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06962941B2 |
|---|
| Source dataset | uspto-grants-2005_11 |
|---|
| ORD ID | ord-0db9fc1e380045ea8d353909bce84b4d |
|---|
| Source note | uspto-grants-2005_11 |
|---|
