Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydroxylamine | HCID 787 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 86585703 | HCID 86585703 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86585704 | HCID 86585704 | — |
Reaction Steps
To 1-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-carboxy-pyrrolidin-1-ylcarbonyl)pentane F-6 (50 mg) in dioxane (1 mL) was added an amine RNH2 (1 equivalent), DIEA (2.5 equivalents) and HATU or PyBOP (1 equivalent) and the solution stirred for 4 h. The reaction was then cooled to 0° C., 50% aqueous hydroxylamine was added (400 μL), and the solution stirred at 4° C. for 8 hours. The crude reaction mixture was then purified by preparative reverse-phase (C18) HPLC to afford N-hydroxy-3-(R)-n-butyl-3-[2-(S)-aminocarbonylpyrrolidin-1-yl-carbonyl)-2-(S)-hydroxypropionamide F-7.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06797820B2 |
|---|
| Source dataset | uspto-grants-2004_09 |
|---|
| ORD ID | ord-7e63e24285054dc0b254bf127dfa5fed |
|---|
| Source note | uspto-grants-2004_09 |
|---|
